One evening last month, I was FaceTiming with my dad. We don’t talk nearly as much as we should so we were getting caught up on each other’s lives. I was mostly telling him about Winnie and her school — about their field trip to the local fire station where Winnie fell in love; the hand, foot and mouth outbreak (I am gagging just thinking about it); and the dramatic day when she got sent to the “calm down corner” which I still haven’t heard the end of. Baby girl was not happy. My dad claims I was the same way as a small child and retold his favorite story of my own meltdown over a broken cookie. Which I personally don’t buy as I am one of the most reasonable people ever.

I’d just gotten back from the far too short, but incredible trip to Spain that I’d taken with Brendan and his parents so we talked about that too. I spent one full day dying from food poisoning in the hotel room — imagine my freak out when I woke up one morning vomiting. It turned out to be razor clams and nothing else and my dad thought this was hilarious.

Then my dad said, “So your mom has been drinking a lot lately.”

“Oh,” I said. This was nothing new to me — my mom has always been a very big drinker. It’s rare to find her without a drink in her hand. I’ve always naively thought nothing of it – It’s always just been the way it is. I mean, she and I would split bottles of Moscato when I was in high school and it was totally normal.

“She said she wants to slow down because she knows it’s been a little out of hand, but she thinks she might need professional help to do that,” he continued.

I didn’t say anything.

“The other night we went out to dinner and she could barely walk. I practically had to carry her to the car,” my dad said.

I burst into tears then. I don’t really know why. I always thought that yes, my mom drinks excessively, but she could control it. The thought of her not actually being able to and admitting that she needs help was so…sad. I just assumed she had a handle on things. I was thinking back to when I was force-feeding her espresso martinis, not knowing that she was literally fighting an addiction. I guess I should’ve known after the way they behaved the last time I was in Houston. I never thought one of my parents would be an alcoholic. My mother is an alcoholic.

“I know,” my dad said after letting me cry for a bit. “Hopefully she’ll be able to get the help she needs.”

It was so depressing. Every time I spoke to my dad, he just kept repeating the same sentiments. She’d go out with her friends and overdo it and my dad would have to go pick her up because she couldn’t walk. One night, my parents went out to a live show and she got hammered and actually got them kicked out of the venue. My dad was pissed.

Meanwhile, my mom was acting like everything was absolutely normal and perfect when I spoke to her. When I asked her about the concert situation, she downplayed it like my dad was exaggerating.

“You know how he is,” she said, brushing it off. “He loves a dramatic tale.”

She’s not wrong, to be fair, but my dad isn’t just going to make something up. I didn’t bring up all the stuff he told me, obviously, but kept asking her if she had anything new she wanted to share with me and leaving space for her to open up to me if she wanted to. But she never did.

Eventually I decided to take a trip back home to assess the situation myself. My dad was making it sound really bad and I imagined my mom was putting whiskey in her coffee and chugging Sutter Home minis like the people on Intervention. It became the only thing he wanted to talk about and I’d text him like, “How is she?” and my dad would say, “Not good.” But then my mom would talk to me like everything was normal. So I needed to go see how bad it truly was.

My mom was surprised by my impromptu visit, but she was happy nevertheless. She looked cute and put together — with wide leg jeans and fresh Botox. I was expecting a shitshow, especially since I surprised her. She looked absolutely fine to me. She made reservations for us to have dinner downtown, but my dad was preparing for a work conference so he couldn’t come.

We ordered pasta and a glass of wine each and I pretended not to be watching her intake. She wanted to talk about Brady because he’d been posting non-stop on Instagram like he just remembered his password or something. It’s mostly pictures of and with Caroline which my mom was happy to dissect with me.

“So is she Asian? She kind of looks like she could be Asian,” my mom said as we scrolled.

“I don’t know, but don’t forget she’s adopted,” I said.

“So she doesn’t wear much makeup, huh?” my mom pointed out. “She doesn’t need it.”

I was particularly annoyed by this comment considering my mom is always telling me that I’m not wearing enough makeup. I guess I’m absolutely hideous. I wonder who I get it from!

“I feel like he really, really likes her,” I said, which kind of pained me. “He won’t stop posting about her.”

“Maybe he’s doing it to get your attention,” my mom said conspiratorially.

Obviously that’s the first thing I thought too, but I said, “I feel like he’s been so much nicer since they started dating. I think he’s a lot happier with her than he was with me.”

“He seems confused,” she said with absolutely no evidence.

“About?”

“Everything, but certainly his relationship with you. He barely knows this Cara and he is probably hoping to get you back.”

I could not disagree more. What was she even talking about? We each ordered one more glass of wine, talked about Brendan (she asked which came as a shock since she doesn’t exactly like him) and how jealous I am about his current lifestyle. He’s not back at his company full time and just pops in whenever he feels like it. He hangs out with his dad a ton and they travel and tour historic NYC buildings and test drive new cars and etc. I want to do that with him! And then randomly, I’ll show up to a job site and Brendan’s Land Rover will be outside because he decided to grace us with his presence. I just want that carefree lifestyle. My mom was less than impressed by this and wanted to know where he gets money since he isn’t “working.” I’m like, I don’t exactly know lady, the same way other people with businesses do — which she in particular should know about since she used to partly own a business.

Anyway, we finished our wine and called an Uber to take us back to the house and I thought: this is fine. We each had the same amount to drink and my mom was able to handle moderation so what the fuck was my dad going on about? But then we got in the SUV to take us home and my mom pulled all these little bottles out of her purse and started mixing them in a bigger water bottle. Like a homemade cocktail kit or something. I have never seen her do that.

“Mom, what the fuck?” I couldn’t help exclaiming.

“Reese, watch your mouth!” she yelled at me, but continued mixing her little drink.

“Do you have a problem?” I asked.

My mom batted her eyelashes at me. “A problem with what, honey?”

“What even is that?” I gestured to the cloudy pink drink that she’d concocted which kind of looked like Pedialyte.

“Just something for the ride home. Is that okay with you?” she snapped.

That’s when I was like, yeah. We’ve got an issue. What’s it called — a “functioning alcoholic?” She’s not even always functioning, according to my dad. The fact that was bringing alcohol and whatever else around with her in her purse was such a major red flag.

I burst into tears in the back of the Uber and my mom didn’t say anything for a while. Then she was like, “What’s this about? Brady? Cara? Brendan?”

Ugh.

“No, this is about you! Dad said you’ve been drinking way too much and now I see what he means,” I said.

“That was months ago,” she explained. “I’ve got it under control now. I don’t know what your dad is talking about.”

“I’m sure he’s talking about this, Mom! This is weird,” I said.

“You’re overreacting,” my mom said calmly. “But if it’ll make you feel better, I’ll put it away.”

It didn’t make me feel better, especially when we got back to the house and she transferred her little drink to a martini glass.

So yeah. That’s where my parents are at. After I left Houston, my mom started calling to chat more — possibly to prove to me that she’s fine and sober and doesn’t need help. And I feel bad for my dad for having to deal with her and her issues. My mom said that he’s been staying at work extra late and I’m like, “Wow, I wonder why!” And I feel bad for my mom too because I know addiction is an illness and she is not going to get treatment until she’s good and ready. And that woman is very stubborn. So we’ll see what happens. 

It was only a matter of time before Izzy started joining us for our Thursday-Friday happy hours. It started as a thing Brendan, Miguel and I did (and sometimes Paige, last year) and then Gigi invited herself a few times and now Brendan was out and Izzy was in. She walked in still hitting her vape so I was instantly annoyed by that.

“Is that my shirt, you fucking bitch?” Gigi greeted her.

Izzy looked down at her basic ass cropped white tee and shrugged.

Is that how y’all talk to your sisters/siblings? A few years ago, my friend Kendra lectured me because I playfully called her a bitch over text message. She was like, “I can’t believe you still speak like this. It’s so disrespectful and unnecessary — grow up.”

I was like, huh??? We’ve always jokingly called each other names in our 20+ year friendship, like it was completely normal? She’s always adulted differently than me and I thought she was once again being uptight and ridiculous. But hearing the derogatory way Gigi and Izzy speak to each other is so jarring and…perhaps I’m getting old but I can totally see what Kendra meant. If even I am clutching my pearls then it must be extreme.

I had every intention of grabbing my things and dipping out (there’s only so much of Gigi and Izzy’s squawking one can take), but Miguel begged me to stay for one more drink. I agreed — mainly because I felt bad about leaving Miguel alone with them knowing how annoying and exhausting they are. He’s the one who hired them both so he really shouldn’t be annoyed, but I still felt bad.

Several hours later, I was still sitting there with a spicy margarita in front of me. Admittedly, Gigi and Izzy were annoying me a lot less than expected and I was kind of entertained hearing about bad decisions other than my own. Most of Izzy’s stories involved recreational drug use and sex that didn’t sound 100% consensual. Total pick-me energy. 

She said, “So yeah, we were in LA and tripping bad on molly. I had been hanging out with this producer guy and we all went back to his mansion. He had been telling me he wanted to fuck me all night so I was down for it. And I was pretty much blacked out at that point. We started fucking in his bedroom and his friend came in and put his dick in my mouth. He was hot so I didn’t care, but I was like ‘what is happening??’”

I was like, “Oh. That’s not…great.”

I’m not sheltered at all or anything but I’m always so surprised by people’s casual drug use. It’s just not something my friends and I were ever into. I remember finding out that Brady is a stoner and being so surprised by that because I’ve never even properly smoked weed — not even in high school (nope, too busy giving out hand jobs at football games). There’s no real reason why either — I think I’ve always just been afraid of not having control of my body or actions. Which is crazy considering I drink like a fish which I’m sure some would argue is just as bad.

At this point in the evening, Izzy was standing up next to Miguel in his chair and she was reaching over him to eat the French fries and wings off the plate in front of him. And Miguel had his arm around her waist (which is the move he does right before exchanging numbers/Instagram names with some random happy hour whore). They started going back and forth about Izzy tagging along with Miguel to Queens for something. And I know this is petty, but Miguel said I’m not his type, but Izzy is? Don’t get me wrong, she’s a cute girl but she’s so loud and usually always wrong. And she’s 23. And her lips are overfilled. And her false eyelashes make her look trashy.

“If you want to come with me, you have to finish your drink,” Miguel said.

“I am, I am!” Izzy said.

She still had an almost full glass of some basic girl cocktail (vodka soda with lemon I think) and then when the server came by, Miguel ordered another round for the table.

“Not me, I’m leaving,” I said.

“Already? But whyyyy?” Izzy whined.

“Because I have a child,” I said, which always gets me out of situations with these people.

“K!” Gigi and Izzy exclaimed.

“I think I owe you an email, Reese,” Miguel said. At this point Izzy was glued to his side and had an arm wrapped around his neck. “So if I don’t get it to you tonight, I’ll send it in the morning.”

I was thinking, “Wow, he’s gonna fuck her, isn’t he?” How messy. Don’t shit where you eat! Couldn’t he at least wait until she’d been working there for longer than a few weeks?

“I’m going to need it tonight,” I said, even though I didn’t.

Miguel and Jasmine can do whatever they want in their relationship, I honestly don’t really care, but after all the troublesome stories Izzy had been telling us, Miguel hooking up with her felt particularly gross.

On my way out I texted Jasmine, “Miguel is not behaving!” I had to do something.

Jasmine replied, “Ugh!” but didn’t ask for any details or for me to elaborate. So I didn’t. I was like, this isn’t my business, I’m going to forget this happened and move on with my life. But I was definitely looking at Miguel differently.

And I completely forgot about it as planned until the next morning when Gigi texted our group (I’m for some reason in a group chat with the sisters) and said, “Bitch, are you almost home?”

Izzy said, “Yes, but I’m going to need to stop at Duane Reed 🫣”

Gigi said, “Ugh, you’re such a hoe!”

So wait. If I were following this story correctly, Miguel and Izzy had gone to Queens together after happy hour to do God knows what and now she needed to go to the pharmacy? I hated all of this.

Anyway, I am so overwhelmed by everything I have to tell y’all. Life has been crazy. I guess I’ll just start with Labor Day weekend where I had plans to go to Brendan’s family cabin with him and his family. Brady was supposed to have Winnie that weekend, but a week before he texted me to say that his plans had changed and would it be okay if she stayed with me? Of course I was more than fine with this — I hardly ever get to spend holidays with my baby. I would have to back out of the cabin trip though because as far as I was concerned this was an adults only trip and Winnie wouldn’t even have anything to do while we’re there. But Brendan insisted we both come and that it would be “so fun.” Brendan and Winnie are super close and love each other so I’m not surprised he wanted her to come with us, but I was worried because Winnie hasn’t spent any significant amount of time with Brendan’s family and what if she was annoying or acted like a brat or threw tantrums the entire time? She’s just a child of course so all of this is normal, but there is no one her age in Brendan’s immediate family so I was hyper aware that no one would be used to it.

But it turns out, I was worried about nothing and the cabin trip was absolutely fine. Winnie took an immediate liking to Brendan’s dad (who’s surprised?) and followed him around the cabin to see all the stuff he was doing. And Margo made a comment about how she was surprised at how well-behaved Winnie was being (I always tell her stories of Winnie misbehaving). I was like, yeah same. The internet connection and iPad definitely helped too.

The only issue I had was one evening Brendan and Winnie were sitting on the couch watching YouTube videos together and they looked so fucking cute. My sweet little babies! I love them so much. I got up to take a picture of the scene and Brendan’s sister Danielle, who had arrived separately to the cabin a few hours earlier and hadn’t said a word to me, came up beside me and said, “Aww, Brendan, you can add this to your Hinge profile!”

She was obviously joking, but it wasn’t even funny and at my expense? What’s her problem? I’ve come to terms that Danielle and I will never be friends, but still, it was uncalled for. Couldn’t she at least pretend she didn’t wish Brendan was still with his bitchy ex-wife? I turned and gave her a look — the same kinda look Jada Pinkett Smith gave Chris Rock right before Will Smith went on stage and slapped him, what a moment in time — but I was not about to give her the satisfaction of a big reaction. She’s such a bitch. Like Brendan would ever even be on a dating app!

I didn’t think Brendan even heard her and was mostly just curious to see how the picture turned out (adorable, ofc). And Danielle fucked off after that and didn’t interact with me or Winnie for the rest of the evening. I think Brendan has realized that me and his sister don’t get along as well and he doesn’t try to force it.

However. The next morning we all sat outside on the deck and ate the beautiful breakfast spread Margo put together. Afterwards, I was in the kitchen alone, minding my own business, and Danielle came in and cornered me. Mind you, she hadn’t spoken a word to me since arriving.

“Heyyy,” she said to me.

“Hi,” I said back.

“I wanted to apologize for my joke yesterday. I hope you know I wasn’t being serious,” Danielle said.

“Oh, it was a joke?” I said because aren’t jokes supposed to be like, funny?

“Yeah. I was being funny.”

Fascinating! “Oh.”

“Yeah, I wasn’t trying to offend you.”

“Okay. I wasn’t offended,” I lied. What was I supposed to say? Obviously Brendan sent her to apologize because he didn’t want there to be any tension. I was happy to pretend everything was fine and go back to ignoring each other.

“Okay, good. I just wanted to make sure,” Danielle said.

“K,” I said and that was that.

Sorry this is so short, but I’ll be back soon. I have so much to tell you about my mom, Brady, Cara and Winnie.

I’m sure no one is surprised to know that Winnie ended up at the school I chose, not Brady’s. No matter which way you looked at it, it made zero sense for her to go to school in Connecticut, but Brady enjoyed fighting with me too much to admit it. Eventually we agreed to send her to the school near our apartment in the city and we’d split the cost. I think Brady realized he didn’t have much of a choice since he hadn’t communicated with his school since January and the deadline for enrollment had already passed. Which only proves my point that he only wanted to fight with me and hadn’t even attempted to sign her up for his school.

Anyway, once everything was finalized, I felt a lot better. And now I had other things to worry about like if Winnie was going to be heartbroken that she’d be away from all of her daycare friends or the fact that I’d already need to take her out of school for a few days while I went on vacation or the headshot the school requested that they wanted to use for the classroom.

Headshot? I was like, wait do I need to hire a professional for this? How serious should I be taking this?

“You could probably take a decent picture on your phone,” Brendan suggested.

So I took this idea and ran with it and set up a photo shoot in the apartment. We’d do one scene using the soft white wall living area wall as a the background and Winnie would wear a pale blue button down and her baby-fine hair would be brushed and parted down the middle (she hates having her hair brushed) and I was crying because the picture looked like it belonged on LinkedIn. She’s so freaking cute! 

We moved to her room and took more pictures using her pink bedroom wall as the background and she wore a beaded headband and a little pout. Brendan even got in on the fun and started directing and helping with angles and lighting. And rambunctious Winnie, who is usually doing screaming laps around the apartment around this time, sat patiently while we tried to get the perfect shot. She’s never patient while we do anything. Had she found her calling? Was this her first foray into a modeling career?

Next, we used the cityscape outside the window as a backdrop, but Winnie started getting restless at this point and wanted a snack. But that was fine because we’d taken a zillion pictures so surely one of them would be good enough to submit to her school. My little amateur model!

Winnie’s school was having a child-free orientation one evening before the school year began to get to know the teachers and meet other parents. The invitation mentioned wine. The orientation happened to fall on my birthday so Brendan and I were going to go together and then go out to celebrate my birthday after. Winnie would stay at home with her babysitter, Claire, a 26 year old yogi who works in fashion. I found Claire through one of Brendan’s stepmom’s friends and she always tells me things that make me think, “Hmm, maybe I shouldn’t leave my child alone with this young lady.” Like, “When my friends and I used to do coke all the time, it was so bad. One time my nose started bleeding in the middle of dinner at Lola—” I know everyone in New York does coke, but still. And Winnie really loves her and nothing bad has happened so…I suppose it’s fine.

I sent Brady the invite assuming he wouldn’t be able to make it since it was on a weeknight. You know how he is. He can’t leave the hospital before 8 PM or everything will fall apart. Plus he hadn’t really been involved with her school thus far so I didn’t think he’d suddenly start now.

He just liked my message and didn’t reply, but then the day before the orientation, he texted me saying, “Are you okay if I bring Cara? We have plans after.”

Ew. What plans did they have on my birthday? And why wouldn’t I be okay with his very new girlfriend being there? If they are truly as serious as Brady is (suddenly) making it seem then I expected her to be around and it was obviously okay with me! My only issue was that the relationship seemingly came out of nowhere and then Brady immediately made sure I knew and I don’t know, it just seems like after I told him I didn’t want to get back together and work on our relationship, he found the nearest 28 year old to throw in my face.

So I replied, “Fine with me.”

It didn’t seem like anything I needed to warn Brendan about beforehand. It’s not like Brady and I have some crazy tense relationship that needs a warning like Brendan and his ex. Brady and I are amicable and we see each other weekly and of course he would be at his daughter’s school function. And I wasn’t going to bring up the girlfriend because does she even matter? (Also last time I did I had a meltdown and I didn’t trust myself).

So Brendan and I got dressed and walked over and we were greeted immediately with glasses of sparkling rose. I knew I liked this place. For some reason I was really excited to meet all of the other parents and see what they’re all like. I went up and introduced myself like, “Hi, I’m Reese, Winnie’s mom and I’m a project manager. This is my cute boyfriend, Brendan, who isn’t Winnie’s dad. Don’t ask what his job is because he doesn’t currently have one — tell me about yourself!”

The headshots were posted everywhere — huge on the whiteboard, at their little desks, in their cubbies, as magnets on the door. I’m so glad I actually put effort into Winnie’s because obviously hers was the best. I lost count of how many times people came up to me and asked if she’s in modeling (including the teacher) which Brendan and I found amusing. It’s like, “No, we just took these pictures on the fly — I guess my kid is a natural!”

All of her new classmates are adorable though. Like the twin girls whose parents are an influencer and a stay-at-home dad. I hoped Winnie would become friends with them. And the adorable boy wearing a turban in his picture (he’s so cute I screamed) whose parents I’m pretty sure are billionaires. I also hoped Winnie would become friends with him.

Eventually, Brady and Caroline wandered in. I was a couple glasses of wine in and forgot they were coming. Caroline clocked us immediately and waved enthusiastically as they made their way over. Neither of them had wine (odd). Do you know those people who don’t pick up their feet all the way when they walk and they just sort of shuffle them and so their shoes make a ton of noise? That was Caroline. She was wearing chunky loafers and I could not believe she didn’t notice how loud her walk was.

“Happy birthday, Reese!” she said.

How did she know it was my birthday? Obviously Brady must have told her, but do you think he wished me a happy birthday? Negative!

“Thank you!” I said back. What a sweet girl! So then I felt bad for judging the way she walks. “This is Brendan.”

“Hi, I’m Caroline!” she said all happily as she shook his hand. “Or Cara.”

“We’re going to walk around,” was all Brady said.

Uh, okay? Hello to you too? Why was he acting so annoyed and over it? If he didn’t want to come then why did he?

“Do you want me to introduce you to the teacher?” I asked, but Brady was already starting to walk off.

“I’ll find her,” he said dismissively. Caroline (loudly) followed him.

I could not believe how rude he was being! Brendan turned to me and smiled encouragingly like he knew I was trying and like he wanted to ask if I was okay, but knows I hate that so he couldn’t.

What the fuck ever! Anyway, we walked around a bit more and met a judgy gay couple who I think hated me (crazy considering most gay people love me) so I guess I wouldn’t be friends with them. They’re like, “Oh, where was your daughter before? Weird, we’ve never heard of that school. Oh, it’s not really a school? Was that by choice?”

Eventually, we decided we’d stayed long enough and that we could get going. Our dinner resi wasn’t for another hour, but we figured we could get drinks beforehand. It was my birthday, after all, so it was only right to get drunk and celebrate. I had every intention of Irish goodbye-ing Brady and Caroline after the way he acted earlier, but then they came marching/shuffling over.

“Is she wearing makeup in that picture?” Brady asked, gesturing to one of the blown up headshots in front of us.

And I don’t know why, but I started uncontrollably laughing. Makeup? She’s 3?! And was he so unfamiliar with our daughter’s appearance that she took one good headshot and he suddenly thought “Toddlers and Tiaras?” Ridiculous! And since I couldn’t stop laughing, Brendan started laughing too and Brady and Caroline just stared at us expressionless.

“Ugh, no! She’s three!” I finally said.

“Okay,” Brady said.

So then I was annoyed at him for even thinking I’d do that and for looking at me like I’m fucking stupid.

“There’s wine, you know,” I suggested because those two needed to loosen up.

“Oh, no thank you! We’re having dinner with my parents and you know…” Caroline said happily, shrugging.

No, I didn’t know.

“Oh,” I said.

“But any other time, for sure! My parents don’t really drink that much so…” she continued. Was she capable of completing a sentence?

“I don’t think I could survive dinner with my parents without wine,” I said and Caroline giggled.

“No, I for sure get that!” she said. “My parents are really great though. I’m adopted and—”

Adopted? I had no idea that Caroline was adopted. My mother would have a field day with her. Naturally I was intrigued and wanted to know more about her life and I found out that she was raised in Connecticut (Brady is so obsessed with Connecticut that he even found his girl there) and that she has a fairly big family that she’s close with.

When she said where in Connecticut she is from, Brendan asked which school she went to and the two of them started discussing people they both know. Like, “Oh, do you know Rebecca So & So? We all went on a class trip to Germany together.” So I was obviously annoyed by that — who cares if you know the same random people? I bet neither of them even talk to Rebecca So & So anymore.

Then Caroline was talking about how she’d gone to university in the city somewhere so they started talking about the people they know at that school and even Brady chimed in a few times since he’s met some of Caroline’s random friends or I guess they know the same people. Eventually, I asked Caroline what she does for work even though I hate that question because I was otherwise not included in the conversation. I assumed she worked in the medical field in some way since she was wearing scrubs that one day.

“I’m a nurse anesthetist,” she said proudly. “Do you know what that is?”

I started to say, “I don’t care,” because I don’t and I could Google it later if necessary, but that’s rude so I just said, “I don’t.”

So she took it upon herself to explain to all of us the day to day duties of her job and the only thing I took from it is that she works in a hospital. Brady loves a coworker/nurse!

“So is that how y’all met?” I asked, delighted and fascinated. I certainly couldn’t judge either of them for dating someone from work, but Brady doing that was so funny to me.

“No,” Brady said, like he was offended.

Caroline said they met “through friends” which to me is code for online. I can’t imagine Brady using Tinder or Hinge or whatever app the singles are using these days, but I could see him on Match.com or something.

“So do you have fun plans for your birthday, Reese?” Caroline asked. Deflection so I wouldn’t ask for more information!

“Actually yes. So we’re gonna leave,” I said, purposely vague. “I’m glad you both could make it.”

“Same! This was so great,” Caroline said.

Brady said, “Bye,” and then that was it. Such an ass!

On our way out, Brendan asked, “Are you good?”

Usually I don’t like when Brendan checks up on me like I’m some unstable child, but I actually appreciated him asking me because I wanted to discuss.

“I don’t know why Brady was acting like that. Wasn’t he being so weird?” I said.

“Yeah,” Brendan agreed. “But is he always like that or do you think maybe it was uncomfortable for him?”

“Why would it be uncomfortable? It was fine! He had no reason to be an asshole except that he thinks it’s fun,” I said.

“Yeah,” Brendan said again. “I don’t think he was that bad though.”

“I do! And he didn’t say happy birthday to me which was obviously deliberate — even Caroline did!” I went on. “Not that it even matters, I just think it’s inconsiderate! He randomly decides to make things tense and I’m sure next time I see him he will act like everything is normal.”

“Yeah,” Brendan said for the third time and added nothing else, so I figured I’d better stop and just enjoy the remainder of my birthday.

Since Brady wasted no time flaunting his new girlfriend in front of me, I was no longer going to try to hide my relationship to spare his feelings. Not that Brady has any feelings and not that I was hiding anything in the first place. I wasn’t inviting Brendan to pick ups and drop offs because that seemed unnecessary, but why shouldn’t I? I’d argue that he’s a bigger part of Winnie’s life than Caroline is. And I have millions of cute pictures with my boyfriend, perhaps it was time to plaster them all over my socials to show them off? Maybe I should send Brady and Brendan out for a coffee date to get to know each other since we’re all going to be a big happy family now?

I didn’t do any of that. Brendan’s schedule doesn’t even allow for him to accompany me to drop Winnie off because he’s always doing stuff on Saturday mornings. You know Brendan. He’s at a gym class or at cryotherapy or on a boat or doing a favor for his stupid sister. And anyway, if I started bringing him around all of sudden now, it would seem like I was doing it out of spite (and I would be). And as much as I wanted to show Brendan off to all of my nosy followers, I’m just…still not ready. And I’d never tag him — can you imagine? My friends would go to his wide open profile and find him posted up with a teeny tiny blonde (not me) aka “the love of his life.” Maybe once those pictures are gone, I’ll consider it.

Once the summer was in full swing, Brendan’s little early retirement began. He was like, “I’m just going to take a few weeks off,” put an out of office message up and then ghosted us. Well, them — at the office, not me. He’d call me on a Tuesday morning and be like, “My dad and I are flying to Maine for the day, talk to you laterrrr!”

I was thinking, “It must be nice to take an undetermined number of weeks off of work to do whatever you want!” But I was happy for Brendan and sad for myself.

Anyway, Miguel ended up hiring Gigi’s sister even after I advised him not to. She just graduated from college and hasn’t been able to find a job so to everyone it made perfect sense for her to just walk into Brendan’s company and start working. And obviously I was skeptical. Gigi had been inserting herself into everything and like I mentioned before, she’s kind of annoying so she was enough for me. Adding her sister to the mix was going to create chaos, I just knew it. Gigi invited herself to happy hour one Thursday afternoon and went on and on about her sister (Izzy) and how much we’d all like her. Which then got us on the topic of previous work experience and how they each chose which college to go to and their family life. She talks so fucking much. I know I talk a lot, but this was a bit much.

I’ll be like, “Miguel, how was your weekend?”

And Miguel will say, “It was good, I tried a new dinner spot in Brooklyn.”

And Gigi will interrupt and say, “Oh really – what’s it called? Because I was thinking of going to Brooklyn for dinner, but I didn’t end up wanting to go all the way over there so me and Izzy went down to the East Village and then we wanted to go to this rooftop, but the line was too long and my promoter friend…”

In my opinion, there’s never any point to anything she says. What? I know it sounds mean, but she always interrupts everyone to say absolutely nothing of importance. It’s like, I want to know about Miguel’s dinner date in Brooklyn, not your promoter friend!

Izzy was hired to work with Yesenia, the sweet young lady who handles all of the admin work for Brendan’s company. I adore Yesenia, mainly because she always tells me everything. Like this one time, she told me that Miguel had expensed $3,000 worth of shit for his little office and should she tell Brendan? I’m like, “That’s totally your call, but yes you should tell him.” But it’s mostly screenshots of the married men from their team flirting with her. And we both agree that it’s inappropriate, but she enjoys the attention and I’m entertained so we keep it a secret.

So anyway, I’ve always liked Gigi. She’s fucking annoying, but she’s sweet and she’s not malicious — she’s just insufferable. And when I met Izzy one day at their office, I immediately liked her too. Gigi and Izzy are both really thin and tall — but not supermodel tall, they’re both like 5’8. And they’re both pretty in an approachable kind of way. Like not overly hot, but you’d still do a double take. On the day I met her, Izzy was having a meltdown because she had a trip to Paris planned, but hadn’t received her passport in the mail yet.

“See, this is why I told you to get it months ago, you stupid bitch,” Gigi said to her.

Oh?

Miguel looked at me and shrugged like they do this all this time.

Later on, Izzy came up to me and said, “So how old are you?”

It was actually quite rude, but I’d give her a pass since she’s only 23. We started talking about her trip to Paris and I was giving her recommendations (don’t forget, I went to Paris once and now I’m an expert) and she kept saying she didn’t want to do the things I suggested because she’s far too anxious. All of her mannerisms are kind of skittish — like a cat or something — so I could see it. She did, however, talk about how she wanted to visit the Chanel flagship and how she had an appointment booked at Hermes. I’m like, okay she’s fun in a flighty kind of way. The same way I was at that age. She was barely employed, but about to spend $4,000 – $8,000 on a bag. Love that for her.

The best part is the fact that I’ve rarely seen Brendan annoyed by anything or anyone (he has the patience of a saint), but whenever Gigi and Izzy interact, he gets visibly agitated and retreats. I get it — they are so loud and their vocal fry is unbearable — but it’s very funny. Maybe that’s what finally sent him on his sabbatical!

And to say Yesenia was annoyed by them would be an understatement. At first I thought she was being nit-picky. Like, “Izzy walked into our meeting 7 minutes late with an iced coffee,” and “I’m going to kill her, she canceled our training to go on visits with Gigi and Miguel.” Or my favorite, “Izzy just told the entire office that she had sex with her ex last night and he came inside her so now Gigi is taking her to get a Plan B.” Nothing egregious I guess, but I could see why Yesenia was put off by her.

And then Gigi added me to a group chat between her and Izzy to ask a work related question, but then the group chat turned into them sending outfit pics, complaints about the Starbucks barista, and mindless observations about Miguel, like “I’m pretty sure he has a hickey on his neck lolz.” I was wondering, “How did I get in this?” But I was too polite to leave the chat, knowing they would be alerted.

Eventually Yesenia had to put her foot down because she actually did need Izzy’s help doing things around the office. I told her that she needed to be super direct with Izzy and give clear directions with a deadline. Trying to be nice and using the royal “we” was not going to work with this girl. Yesenia sent a screenshot of Izzy’s message back saying, “That’s impossible. Even if that’s all I worked on for the next 48 hours, I wouldn’t get it done. Not happening.” And then another from Gigi saying, “Izzy is working with Miguel and me on this really important project. She can help you with your thing starting next week.”

Do you know what I was going to do? Nothing! I was going to mind my own business! I’d tried to offer my best advice and it didn’t work so I was going to move on! None of this had anything to do with me and I wasn’t going to bother Brendan while he was away with these petty issues.

Carly texted me one afternoon to let me know that she and Chris, her husband, were coming to New York for a night to see a show. Carly is my good friend from Chicago who now lives in Philadelphia with Chris and their daughter.

“I think Chris said we’re grabbing dinner with Brady beforehand so please come! I’m dying to see you!” Carly said.

So Chris and Brady used to live together in Chicago and it’s how I met Brady in the first place. You can read about that here. Despite us all living just a few hours from each other, I haven’t seen Carly in over a year. We’re both really busy, but also something about her is depressing to me so I avoid keeping up with her.

I texted back, “Yeah, I’ll let you know about dinner,” knowing that if Brady was going to be there, I would absolutely not be there. Why would she even invite me? And why were they choosing Brady over me? Carly is well aware that we broke up and I would think she would ask me to dinner before asking him.

Needless to say, I didn’t get back to her about dinner because I wasn’t interested in going. I did, however, text Brady to talk to him about it.

“Yep,” he confirmed. “Excited to catch up with Chris.”

Whatever! I hoped they all had a terrible time!

Carly called me the day after they all had dinner while I was driving to drop my child off with her dad. I felt kind of bad about ghosting her, but not really.

“We missed you last night,” she said in a sing-songy way.

“Oh, did you?” I said back sarcastically.

“Totally, but Brady brought his girlfriend. Cara? I get why you didn’t want to come. I didn’t know he was dating someone,” Carly said.

Oh??? Now I was interested.

“Yeah, they’ve been together for a few moths. What did she say?”

“Nothing, she was really sweet. I can’t believe she’s 28.”

28?! It never even occurred to me to wonder how old Caroline is because I assumed she was around my age, but 28? Seems a little young for Brady who turns 36 this year (I can’t think about this for too long or I’ll spiral). No wonder she seems so optimistic, she’s still so young and unjaded!

So I made Carly tell me literally everything that happened including what everyone was wearing. She had the nerve to say that Caroline is “like us.”

“What does that even mean? She’s nothing like me,” I said.

“Like fun and open-minded. I don’t know, she seems cool,” Carly explained.

What was this girl even talking about? I have no issue with Caroline, but why was Carly acting like we were all going to hold hands and be best friends? After one dinner? I was annoyed by the entire thing.

After I met Caroline that one Saturday morning, she was everywhere. We broke the seal and now she was able to come out of hiding.

It started on Sunday, when Brady posted a photo of them together on Instagram. On his actual feed. And she was tagged. Hard launch! Brady hasn’t posted anything in like four years so this was quite surprising to me. And he’s not very Instagram savvy so he doesn’t realize that posting pictures of his new girlfriend while still having pictures of his ex-girlfriend (me) posted is tacky. Is this a straight man thing? Because Brendan still (still!) has all the pictures of his ex-wife posted. Even after I confronted him about it! Just delete them already. Or if you want to keep the memories, archive them. God. I don’t get it.

Anyway, in the picture, they’re sitting outside at a restaurant overlooking a body of water and his arm is around her. It was probably taken in Boston, I guessed. Brady was wearing sunglasses and a smirk — the knowing kind of smirk he does, like he knew I’d see the picture and start snooping. I wanted to slap him! Caroline was also in sunglasses and her hair was draped perfectly over her shoulders like a news anchor.

Her page is private which is perplexing to me because who has a private Instagram in 2023? What are you hiding? Her profile was like: 

A portrait standing fully clothed on a beach

Caroline 🐱

Cheesy manifestation quote 💫

Ooo, mysterious! And basic!

Brady texted me later that night —  way later, it was almost midnight. I was awake in bed, sending TikToks to Kristina and obviously I thought the worst. Why else would Brady be texting me at such an hour?

He said, “So what percentage of school did you plan on paying?”

I assumed Brady was going to pay for all of it. Or most of it at least – because that’s what he told me a while ago. What? He’s the one with the money — I wouldn’t want to go bankrupt trying to send my kid to school! And I pay for all of her clothes and toys and beauty products and her dance classes so why wouldn’t he?

“What percent do you think is fair?” I texted back.

“Since the school is your choice, I think at least 75% 😊” Brady said.

It was the emoji for me. When has Brady ever used an emoji?

“Hilarious! Have they approached you about joining SNL yet?” I said back.

“Not yet, but I bet if they did I could afford that school.”

So funny. I sent an eye rolling emoji back.

Then he said, “Seriously, did you plan on helping pay for the school?”

Ugh.

“I guess, but I’d like to remind you that you agreed to pay and I didn’t bank on you going back on your word, Brady,” I said.

“That was before you chose the most expensive school you could find, Reese,” he said and then added another smiling emoji.

“I wasn’t given a budget,” I pointed out, which is true.

Brady ignored my valid point and said, “50/50 seems fair to me.”

Ughhh.

“Considering I’m going to be the one who has to get her to and from school everyday, I handle her dance classes and all of her doctor’s appointments, and buy all of her clothes and toys, I disagree. But we can discuss it further next week,” I said.

Brady said, “I assumed you’d use the money I send to you every month for that. Plus I’m covering health insurance and your cell phone bill.”

I wasn’t trying to get into the nitty gritty details so I was like, “I said we can discuss it next week!”

Brady said, “Okay.” And then, “Are you in bed?”

I replied, “I am, are you?”

“Alone?” he said.

I looked around my dark bedroom, just to make sure. Where was this going? “Yeah, why?” 

“Me too,” Brady said. And then in a separate text added, “Talk to you next week.”

Uh…okay? What a strange line of questioning.

On Tuesday morning when Brady dropped Winnie off at my apartment, I thought maybe we’d talk about it some more. I was gonna be like, “And why does it matter if I’m in bed alone?”

Except he was being super short and barely even said hello. Not this again. He’s so hot and cold with me. As I was getting Winnie out of her booster seat, I saw that Brady’s phone was mounted on the dashboard and he was on an actual live phone call with Caroline 🐱. I guess he had it muted or something, but no wonder he didn’t want to chat.

Oh well, that had nothing to do with me. I pretended I didn’t notice we potentially had an extra set of ears listening.

“Do you want to continue our conversation from the weekend?” I asked.

“Not now, I’m in a hurry,” he said dismissively.

“Okay. I’ll text you later then.”

“Bye Daddy, I love you!”  Winnie squealed and then we sent him on his way.

Brendan came over later that evening. We hadn’t hung out in like two weeks and he was all tan from spending so much time in Florida. Winnie was excited to be reunited with her bestie and had a ton to fill him in on (mainly her new set of dolls since she dismembered and graffitied her old ones — she’s in her destructive era). As soon as he sat down on the couch, she immediately started climbing him like a piece of playground equipment like she always does.

“Oh my gosh, so tell us about what you did in Florida,” I said. What I really meant was, “Did you run into Reagan while you were there?”

Meanwhile, I got a text from Brady. It said, “Are you ready to be reasonable?”

Excuse me?

“Do you think I’m being unreasonable? You’re the one who said you’d pay for Winnie’s school!”

Brady said, “I may have, but I’m not paying that much. So if you really want her to go there then you’re going to have to get over that.”

Uh, okay. What an asshole. Next to me, I could hear Winnie getting more rowdy and I told her to calm down.

“Yeah, be careful or you’re gonna hurt yourself,” Brendan said.

If this child ended up in the ER, I was going to kill her.

Brady texted me again when I hadn’t responded with another smiling emoji.

😊

“Obviously I’ll help pay for school, but you’re being really annoying. You should’ve never said that if you weren’t going to follow through,” I replied.

“Me? You’re the most annoying person I’ve ever met. 😊” he said.

These fucking emojis!!! I was typing back a scathing response because why the fuck was he even bothering me? I said I would text him! And I had company over that I needed to focus my attention on. Speaking of which—

Brendan let out a loud, weird yelp and I looked over to find him doubled over on his side like he was in pain. Winnie was still sitting on top of him and she looked delighted with herself.

“What’s going on?” I asked, completely oblivious since I wasn’t paying attention.

Brendan was literally like, groaning in agony, but managed to let me know that Winnie had punched him in his crotch area. Punched?! And she was still sitting on him proudly like she just climbed a mountain. It was totally not funny, but it was kind of funny.

“Winnie!” I exclaimed.

“I didn’t mean to,” she said with a big grin which was not at all convincing.

“You should still apologize,” I said. “And maybe you should give Brendan some space. Like, do you need ice or something?”

Brendan tried to laugh and shook his head no. What? I don’t know! 

I went to pick Winnie up off him and she screamed “I didn’t mean to!” before bursting into a fit of tears. Seriously?

“This is not how someone who ‘didn’t mean to’ reacts,” I said which sent her over the edge. Drama queen! It was already close to time for her to go to bed anyway so I let her cry it out until she fell asleep.

So I felt bad about all of that. Brendan assured me that it was fine and he knew it was an accident. I was thinking, “Was it? How can we be so sure?” I mean, the tantrum was the act of a guilty child, but how would she even know doing that would elicit such an extreme response? It’s not like she’s ever done it to me.

I chalked it up to them just playing rough until I texted Brady back later. He’d texted me a few times after calling me “the most annoying person he’s ever met [smiley]” The nerve. He said:

“Maybe not the most annoying, but you’re pretty far up there.”

“But you do it on purpose though, don’t you?”

“So how much of school were you planning on covering? 50/50?”

“Sorry, Winnie punched Brendan in the balls so I had to deal with that,” I texted back.

Brady said something like, “Yeah, she’s been doing that.”

So I was, in fact, raising a little demon. I knew I wasn’t going crazy. Naturally I blamed Brady because this was his fault. She’s been going around punching people in their dicks and he didn’t think to warn me? And was he even disciplining her effectively if she’s “been doing that”? Why was she still doing it?

“You’re on your phone so much,” Brendan said later in bed.

“Sorry, just googling to make sure you’re still going to be able to produce children!” I said and then put my phone away for the night.

On Saturday, Brady offered to pick Winnie up in the city instead of me having to drive to Connecticut. I wasn’t going to argue with that because it was easier for me. Brady texted me to let me know that he’d arrived so Winnie and I headed downstairs. He was sitting there waiting in the car with Caroline. I was like, “Oh, so this is what we’re doing.” He was just going to parade his new girlfriend around everywhere any chance he got — after he’d been texting me literally all week!

“Hi Reese!” Caroline greeted me before Brady even said anything.

“Hi,” I said back.

She spun all the way around in her seat so she could watch me putting Winnie in her booster seat. “Do you have fun plans this weekend?”

“I do, do you?” I said back.

“Yah, it’s my cousin’s baby’s birthday party,” she said.

Brady was looking at me in the rearview mirror like he was trying to see how I was going to react.

“Aww!” I said.

“And I know Winnie likes swimming so she’s going to love the pool!” Caroline said.

“That’s literally so fun.” As you can see, I was really trying.

She said, “I know! It’ll be a good time. We can try to send pictures if you want.”

Wait, did I like Caroline? She seemed so sweet. Where did Brady find such a nice girl and what did he want with her? He’s such an asshole. I was like, you poor thing, he’s going to ruin your life. As my mother would say, bless her heart!

It was probably a coincidence, but Brendan was really busy when we got back from Houston. There was a work event for Danielle, a friend’s birthday dinner, a concert with Kendall (who even goes to concerts anymore unless it’s Beyoncé?), a work trip to Florida and then a separate trip to Florida for “fun.”

Florida is the bane of my goddamn existence. I hate her so much. And I always side-eye Brendan when he takes these little trips to Florida. Remember when he said that he and his ex-wife spent a lot of time there because her family has a vacation house? Why was he so eager and excited to spend time there now? What is there to do? He was posting pictures on boats and fishing and other things that don’t even seem fun and could easily be done not in Florida.

And I’ve been trying not to, but I ended up on Reagan’s Instagram and she was also in Florida at the same time as Brendan and posting bikini pictures. Well, she was tagging places like “The Best Place on Earth” and stuff, but I knew from the pool and lounge chairs that she was at her family’s Boca Raton house. Obviously Brendan wasn’t meeting up with her, but I still watched her stories closely to see if his arm or shoe showed up in the background. Like any sane girlfriend would.

Her stories were like: 

• A full body bikini shot
• A laying down bikini shot
• An açaí bowl
• A full body mirror selfie (in a different bikini)
• A heavily filtered picture of the pool
• A full body mirror selfie dressed for dinner (in designer head to toe – so much for quiet luxury!)
• A photo of her looking bored at the dinner with an untouched plate of pasta in front of her
• A video of her laughing and telling an inaudible story to or about the people she was with

While I was tapping through her story for the billionth time, a text from Brendan popped up.

“What are you doing?” he asked. Like he knew!

Anyway, I had other stuff going on so I shouldn’t have even been worried about any of that. Brady and I have been talking about sending Winnie to school in the fall for months. Like real school where she’d have a classroom and a schedule and a backpack and everything. I cannot believe my girl is getting so big! If I think about it for too long I start to spiral into an existential crisis.

Obviously each of us had done our own research and I found a school that was perfect. It’s only a few blocks from our apartment so we can walk and she’d go Tuesday through Thursday and get out with plenty of time to eat and nap before her dance class in the evenings. Brady was trying half-heartedly to get her into a school near him in Connecticut, but we all knew that wasn’t going to happen. It didn’t make any sense for her to attend school in Connecticut — not with our loose custody schedule or with Brady’s work schedule. He’d have to drastically reduce his working hours and I just can’t see that happening. I also argued that Winnie would experience so much more culture and diversity by going to school in the city. Brady, clearly offended, informed me that there is plenty of culture and diversity in Connecticut. I sent him a screenshot from the Connecticut school’s website where the pictures they posted showed exclusively blonde hair and blue eyed children. Which is fine obviously (Winnie has blonde hair and blue eyes) and I’m sure all of those children are absolutely lovely, but you know what I mean. So I was trying to get him on board with my school mainly because I needed him to pay for it.

One Saturday morning, Winnie and I slowly made our way to Brady’s house. We’d already been to breakfast and every floor in Nordstrom and now I was ready to ditch her for the weekend. I didn’t have any plans, but my child is exhausting.

We let ourselves in (as we always do) and I shouted at the top of my lungs, “We’ve arrived!”

Brady was probably upstairs in his office working so I wanted to make sure he heard me.

Out of thin air (the living room), a girl appeared.

“Hi, I’m Caroline!” she ambushed me. “Or Cara.”

I barely had time to even think about it, but I figured it was her. I was caught off guard because I had in my mind that Brady would never let me meet Kara/Cara/Caroline because you know how he is. “Drama” avoidant. She was dressed in scrubs, like the cute fitted ones people are wearing now, and was actually strikingly pretty. Prettier than I expected, I guess? I figured Brady would go for another mousy girl like his ex, Anna. Like Winnie mentioned, she did indeed have beautiful hair. It was really thick and full and shiny and perfectly blown out. Dare I say, princess hair?

She stopped close to me, right in my personal bubble, and stuck her hand out to shake mine in a way that felt aggressive. I was wearing a tank top and shorts (it was really hot that day) and I saw her glance quickly down at my boobs.

“I’m Reese,” I said, shaking her hand.

“Hi Winnie!” she said.

Winnie ignored her entire existence and threw her bag filled with dolls and toys on the ground before calling out for her dad. Brady came bounding down the stairs and Caroline picked up Winnie’s bag and disappeared to put it away. He was wearing glasses and looked kind of cute.

“Hey,” Brady said to us. He picked Winnie up and they hugged and greeted each other and then he looked at me like, “You’re dismissed.”

Uh, excuse me? I was absolutely not dismissed. I almost always stay for a chit-chat when I drop Winnie off so what was this? Why was Caroline even there?

“I need to talk to you,” I said. I had a folder with all of Winnie’s new school information in it (including the tuition) with me and I wanted to go over it with him.

“Right now?” he asked.

“Yes.”

It was so weird. I don’t really know how to explain it. Brady and I haven’t been together in so long, but I still feel like he’s one of the closest people in the world to me. Despite everything that has happened, he still feels like my family and I know him like the back of my hand. I feel like I can do or say whatever I want around him because it’s just Brady? He watched me push a baby out of my vagina, you know? But now with his new woman here in the flesh, he felt like a stranger.

“Fine,” Brady said and we went to the kitchen.

Winnie got herself comfortable and started opening doors, pulling out markers and books and games, and climbing into the pantry for snacks — getting his house properly chaotic like ours.

“Aww, Caroline seems nice,” I said because I couldn’t even help myself.

“What did you want to talk about?” Brady asked, ignoring what I said completely.

Guess we weren’t discussing that! 

So I pulled my folder out and said, “Winnie and I toured this place two weeks ago and she loved it.”

“Did she say that?” he asked as he started flipping through the folder. 

“No, but I could tell.” I described to him the layout of the school with a greenhouse and atrium, the super secure outdoor recess area, the exotic classroom pets, how the lunches look like Pinterest bento boxes, the yoga and music classes and how all the teachers are bilingual and trilingual. I think Brady zoned out halfway through my spiel and just stared at me and my boobs. Were they really on display that much? Maybe I did it subconsciously just to sway Brady a little more, who knows.

“How is this any different than [the school I suggested]?” Brady finally asked.

“Were you even listening? Literally all of it!” God! 

“Winnie doesn’t have a phone. I don’t think she’s going to care if she can put her lunch on Instagram or not,” Brady said. He was deliberately missing the point and trying not to smile.

“Obviously!” I heard Winnie scream-laughing in the other which told me that she was watching a video or playing with Caroline or otherwise preoccupied. “I’m just explaining to you that everything about this place is perfect.”

“Except that it’s in Manhattan.”

“Uh, that’s the best part.” Was this dude for real? “She’s not going to school here and you know it. You wouldn’t be able to drop her off and pick her up in time with your work schedule and I for-fucking-sure will not be driving to and from Connecticut everyday.”

Brady said, “Well, I can’t afford this.” He was on the page with the tuition breakdown printed on it.

I’ve never in my life heard Brady say he can’t afford something. I know that he’s really smart and thrifty with his money and he never buys anything — so what was he spending all his spare money on? And didn’t he just sell his house? I didn’t believe him.

“Are you kidding me? Yes you can!”

“I don’t think my college tuition was even this much. It’s a little ridiculous,” he went on.

“You think your daughter’s education is ridiculous?” I clarified.

“Of course not, but she has years and years of education ahead of her,” Brady said. And then added, “But let me guess — you haven’t considered anything beyond the next twelve months?”

Guess the titties weren’t working!

We went back and forth a little more and he said he was willing to “compromise” on the New York vs. Connecticut thing, but it would have to be a different school because this one was too expensive. I pointed out that Winnie was already in love with this one and her spot was already reserved for the fall. Do you think Brady had taken the initiative to reserve Winnie a spot at his silly little school in Connecticut? No! Because he knew it wasn’t going to happen!

Eventually when Brady hadn’t caved, I decided to bring out the big guns.

“Okay, well if you can’t help pay, I guess I can ask my dad,” I said.

Brady smirked. “I highly doubt your dad is going to pay for this.”

Like he knows my dad so well?

“My dad actually cares about Winnie’s development so he definitely will.”

“Okay. Let me know how that goes,” Brady said, still smirking like he knew exactly what I was doing.

I was totally bluffing about going to my dad for help, obviously, and he’s super frugal so there was no way he was going to help with the cost of Winnie’s school. So Brady was right and I was annoyed by that.

“Winnie, I’m leaving!” I shouted through the house.

“Bye, Mommy!” she squealed back, but didn’t even get up to come hug me goodbye. I could hear the music from her iPad playing.

As I headed to the door, I yelled, “Byeee, Caroline!” to wherever the hell she was.

There were several beats of silence and then she shouted, “See ya later!” back.

I decided to go with Winnie to Houston for the July 4th holiday. My old bestie, Kendra, gave me the idea when she told me she was going to Houston with her family. I’m like, that’s a great idea — Winnie is overdue for some grandparents’ time. She has grown so much even since the last time they saw her and she’s so funny and smart and yeah. I thought it was time! And I guess I was feeling optimistic or something because I decided to invite Brendan. He could try to get out of coming to Chicago with me, but if he said no to this, we were going to have a problem.

So I asked him if he wanted to come to Houston with me and Winnie to meet my parents.

“I would love to,” Brendan said. “Are you okay with me meeting them?”

If you recall, last year I told Brendan point blank that I didn’t want him to meet my parents. He never brought it up again, but I think it sort of bothered him — especially since he was hinting at it months and months later. But I figured Brendan has shared his entire family with me — including his estranged mother — so it was only right that he got to meet my looney parents. We made arrangements and decided that he would stay for the first two days of the trip and then go home so he could spend the actual July 4th holiday with his family. The thought of spending a holiday away from his family is like, impossible to imagine for Brendan and I wonder if he will get over that once we get married.

And when I said Houston, I meant the beach just south of Houston because there’s nothing to do where my parents live. I told my mom my plan and she took it upon herself to book a suite for Brendan and me and another one for herself and my dad, where Winnie would primarily be staying. What? What’s the point of parents/grandparents if not to take your child off your hands?

I was under the impression that my mom had come around to the idea of Brendan, and us being together, but don’t think I didn’t have a stern conversation with her before we left for the trip. You know how she is. I’m like, “Don’t interrogate him, don’t bring up his ex-wife, don’t bring up Brady, don’t talk about money, don’t ask him anything personal, etc!” She acted like I was being ridiculous for needing to “provide a list of rules” but again, you know how she is. I was sure to emphasize how lovely and welcoming Brendan’s family has been to me because I know my mom and if nothing else, she is a southern gal at heart, so she would want to compete over the niceties. And obviously I warned Brendan about my mother, but I felt like I had some leeway since his mom was kind of an asshole to me.

We were all meeting for lunch on the first day, at a touristy little seafood spot near the hotel. Something casual and not too fussy for the first meeting. We’d just have a nice light lunch where my mom could ask whatever questions she had and we could get on with the weekend.

So I was a little surprised when after the initial introductions and we all sat down, my mom said to Brendan, “No one ever taught you to take your hat off at the table?”

I was thinking, she’s startin’. It was the casualist of lunches, it was hot and near the beach and there were screaming children everywhere and dozens of men at other tables wearing baseball hats and she was worried about Brendan? But still, Brendan pulled the hat off and shook out all his hat hair (and he had his summer hair growing out so I didn’t even mind the hat tbh). Winnie found all of this hilarious and sat on my dad’s lap dying laughing. And after all that, I saw my mom wink at Brendan which told me all of this was a test.

We went around the table and ordered with the server including Winnie. My mom took it upon herself to order a margarita pitcher for the table which I had no plans to partake in (it was barely noon), but I thought maybe it would give her something to focus on other than me and Brendan.

Wrong.

She went around the table and poured some for everyone except Winnie who threw a fit when she found out she wasn’t allowed to have any. She already had a bright pink drink that was most likely going to send her into a sugar coma later so I ignored her, but my parents reasoned with her until she calmed down.

And then my mom asked Brendan how old he is.

“34,” he answered.

“And already married and divorced,” my mom said delightedly. She’d clearly been dying to say that.

“Mom!” I screamed at her. She was worried about Brendan wearing a hat at the table, but where were her manners?

Brendan turned to me and calmly said, “It’s okay,” trying to deescalate the situation.

My mom looked around innocently like she wasn’t sure why I was offended.

“K,” I said.

And then she didn’t even give him a chance to explain his situation or anything and just went on commenting how she doesn’t think he looks 34 and she would’ve guessed 30, max. So obviously she just used the “married and divorced” comment as a dig.

Brendan seemed to reluctantly take it as a compliment until my dad started teasing him about how to look older.

“A little facial hair wouldn’t hurt,” my dad joked.

Do you think they ever teased Brady (who is also clean shaven) about having facial hair? Not that anyone gives a fuck about Brady! And why wasn’t anyone telling me how young I looked? I was actually trying!

“I’m glad everyone is treating me like I’m a cougar,” I interjected.

“Oh we’re not, sweetie,” my mom said, brushing me off. “But I do prefer your hair longer though. It’s more youthful.”

A few months ago I chopped my hair off into a bob (I do this every few years for a fresh start) and now it’s grown out to just past my shoulders.

“Well this is easier and healthier. My split ends were starting to cut me, they were so bad,” I explained.

“I think it looks nice,” my dad said, only half paying attention.

“Do you like it, Brendan?” my mother asked.

“Umm.” Brendan turned and looked at me and seemed to study my hair and face combination. If he said no or anything other than singing my absolute praises, I was going to kick his ass and send him on the first flight back to New York.

“Yeah,” he finally said, grinning. “I can’t get over how good it looks.”

“Of course he’s going to say he likes it, Jackie, he’s not rude,” my dad said.

They sat there bickering (which became a recurring theme on the trip) until Winnie said I should have princess hair. Winnie’s current obsessions are princesses and Barbie. She said Kara has princess hair.

“Who is Kara?” my mom asked her, completely oblivious.

“Brady’s girlfriend,” I answered, a bit too excitedly.

“Brady has a girlfriend?” my dad said.

“Oh, he didn’t tell you?” I said, sipping my drink. Brady and my parents love to have conversations behind my back but he hadn’t told them about Kara? Shocker!

“No, he didn’t tell me. Did he tell you, Jackie?” my dad said.

She shook her head no and looked genuinely really surprised which I loved.

“Apparently they’re getting serious. He put his house on the market and I think they’re considering moving in together,” I went on. I could feel Brendan staring at me, probably sensing that I was being messy and speculating, so I didn’t look at him.

“Well that’s unexpected,” my mother said. I wanted to know what she meant by “unexpected” but I’d ask her later, when Brendan wasn’t around.

After Winnie picked what she wanted off her plate and my parents’ plates, she wanted to come over to our side of the table. Then my parents actually started showing interest in Brendan and asking him questions about himself. In true fashion, my dad wanted to know about his education and what he likes to do for fun while my mom wanted to know more personal things like how old he was when his parents got divorced. She was going to try to dig up all his trauma and break him down at the table, but she was impressed when he told her that his parents put him and his sister in therapy after they divorced. Plus, like we all discussed, he’s 34. I don’t think he’s concerned about his parents’ divorce when he was a kid. Personally, I was going to need therapy after watching my parents argue and fight all weekend. They clearly hate each other and I’m just now realizing it.

After lunch, we walked down to the boardwalk amusement park type situation which was as gross as it sounds. I hated every minute of it, but everyone else seemed to enjoy it. Winnie went back and forth between running and screaming down the boardwalk and wanting to be carried by my dad or Brendan.

My mom came up to me and said, with a straight face, “Winnie loves him, at least.”

What the fuck was that supposed to mean? Of course she loves him! She didn’t care if I did or not.

My parents took Winnie for the evening so Brendan and I could do adult things. Meaning: 

1. Go to dinner 
2. Go out for drinks 
3. Get tired at drinks and go back to the hotel to get in bed

The next morning, my parents called bright and early, wanting to go out for breakfast.

“And hurry because Winnie is starving,” she said.

I rolled my eyes. I was not even about to argue with her as she knows Winnie is dramatic about eating in the morning. But still, we got up and dressed. My mom had made some comment about Brendan and me both wearing matching Birkenstocks the day prior (in a way that felt judgy) and not that I cared, but I was sure not to wear them again.

We met them down at the restaurant where Winnie already had a big plate of pancakes in front of her.

“You must’ve been out late having drinksssss,” my mom sang as we sat down. Mind you, it was like 8:30 at this point so I’m not sure why she was insinuating that we slept in or something.

“We literally weren’t,” I said, but my mother ignored me. She wanted to talk about Winnie’s sleeping habits. Ms. Winnie, she informed me, had stayed up until 2 o’clock in the morning and even then she threw a tantrum and had to be forced to sleep.

“I mean, even after the long day we had, this child had so much energy! Dad was thinking about leaving us here and going back to the house for the night! I thought of calling you, but figured you were out partying or enjoying each other’s company,” my mother shrieked.

Really?

“Mom, please,” I said.

She continued on. “And then she woke up at 5 looking for food. Luckily we had some trail mix in the room, but Dad was about to go get her something from McDonald’s. This child can eat! She must be going through a growth spurt.”

“Yeah, I told you she’s growing and eats a lot,” I said. “Brady said he had to take her shopping the other weekend because she grew out of all of her clothes there.”

My mom started rambling on about how one of her good friends has a granddaughter who is a little bit older than Winnie and had a ton of clothes to give away and to remind her to get them to me before we left. That sounded like a lot of hassle so I wouldn’t be doing that. She and my dad started bickering about the logistics of getting the clothing back to New York (my mom said I should check another bag and my dad thought they should ship it to me) and I was mortified because they’d already gotten into it about several other useless things already.

And then out of nowhere, my mom was like, “So Brendan, do you want to get married again?”

I’m pretty sure this was on my list of things she wasn’t allowed to talk about, but I was willing to let this slide because I actually did want to hear his answer. Of course he’s told me that he’s open to marriage again, but I wanted to know what he was going to tell my mom.

“Yes—” Brendan started, but then my mom interrupted him.

“Because you know we’ve had Reese’s wedding planned since 2010. You’d think I’m joking, but I’m not! We’ve always wanted a big wedding for her, in a big church with hot pink roses and a ballgown. Oh! You could do matching dresses with Winnie now—”

“Mom, can you please stop?” I asked politely. Like I’d ever do hot pink roses!

“Yeah, you really need to quit, Jackie. You don’t know what might happen between the two of them,” my dad said.

“Okay, I’ll stop,” she said and then turned her attention back to Brendan. “But what’s your timeline?”

I was about to scream at her again for being weird and inappropriate, but then Brendan said, “I guess get engaged in the next year or two.”

And he said it with no hesitation, like he’d thought about it. Brendan and I talk about getting married sometimes, but never in a meaningful way. We just talk about it like we assume it’ll happen at some point and I know better than to try to force it (it obviously worked out really well with Brady). Plus, he’s been married before so I’m sure he’s not trying to rush into another.

“Wait, really?” I said, surprised.

“Yeah, I guess. I’m not in a hurry. What do you think?” he said.

I was like, “Oh, that works for me.” I’m obviously not in a hurry either, but I loved hearing that he’s thought about a timeline. I have no idea if it’ll come to fruition — I can’t fathom getting engaged to someone I’ve never lived with — but still.

“Well, I’d like to have a say in that,” my dad said, half joking. He’s much less opinionated than my mother, and I think more than anything just always wants me to be happy. 

“For sure.”

We spent the remainder of the day at the aquarium mainly because I refused to do the beach. Winnie was more interested in other people’s empty Starbucks trash than any of the animals or exhibits so that was pleasant. Then she talked my parents into spending $300 on random shit from the gift shop which I insisted they keep at their place in Texas because I don’t want it cluttering our little apartment.

My mom got drunk at dinner and my dad was fuming about it because he knew she was going to do that and he’d asked her not to. They’re both so fucking embarrassing. I was watching them argue at the table like, yeah, I’m literally never coming to visit y’all again.

Winnie clonked out at dinner so we took her back to the hotel room for the night. Brendan was leaving to go back to New York in the morning and we laid in bed talking. I said something like, I’m sure after meeting my parents he can see how I turned out so crazy. He assured me that he didn’t think they were that crazy and said my mom was fun. And he and my dad bonded over golf (if you’re at all interested in golf, my dad will love you), cryptocurrency and day trading, whatever that is.

After Brendan left, we went back to my parents house where we would stay the remainder of the trip. You’d think we were staying with them for longer than 32 hours by the amount of food my mom had stocked for us, but I appreciated the effort. And like I mentioned earlier, Winnie can eat, so I’m sure she appreciated it too.

My mom and I stayed up after my dad and Winnie had gone to bed, talking and drinking wine (the bottle that Brendan gifted them like that gentleman he is). Now that we were alone, she wanted to talk about Brady. Of course. But it was fine because I kind of did too.

“So who is the new girlfriend?” my mom wanted to know.

“I have no clue. Obviously I’ve tried to find her, but haven’t had any luck since Brady is vague with details,” I said.

“And you think they’re going to move in together?”

“Yeah, maybe. Which is insane because they’ve only been together for like 4 months. I just don’t see why else he would sell the house he said he bought specifically for Winnie,” I told her.

“I can’t see Brady doing that,” my mom said, like a know-it-all because she knows him so well. “I haven’t heard from him in a while so I guess I know why now. I might text him.”

It was kind of sad the way she said that, like she’s Allie and he’s Noah. And honestly I was glad that they aren’t having conversations anymore because what else would they have to talk about besides me?

Anyway. I wasn’t going to ask, but I couldn’t help myself.

“So what did you think of Brendan?”

“Oh, I like him,” my mom answered with zero enthusiasm.

“That’s it?”

“Yes, he seems nice,” she said vaguely. “And Winnie adores him so you should be happy about that.”

I was just like, what? Utter confusion. My mother has so many opinions and has no problem letting them be known and that’s all she had to say? She was acting indifferent and I was suspicious. I remember her gushing all over Brady when she met him and she’s been obsessed since. She loved him from the minute she met him, and no offense, but I don’t think Brady ever did anything to warrant such strong feelings from her. Even after how awful and mean he was to me and how his mom treated me, she loves him. And it’s not like I care that much what she thinks, I just thought she’d see how better suited Brendan is for me and be happy for me.

One of Brendan’s friends was getting married in Mexico — a friend from college, not from the friend group he shares with his ex-wife. Meaning I was allowed to go as his plus one — lucky me! Miguel and Jasmine were also going so it turned into a couples vacation with a wedding event thrown in there. We booked rooms at a nicer resort (Brendan likes luxury, remember?) and we headed down there a day early to really take advantage.

“Who the fuck plans a wedding in Mexico in June?” Miguel complained when it was 90 degrees and humid when we landed.

I had packed almost exclusively bikinis so I was unbothered. And I knew Jasmine felt the same since we’d packed together on FaceTime.

“Honestly, thank God for them because I really needed a vacation,” Jasmine said.

Jasmine is allegedly a model, but I’ve literally never seen her work so it’s unclear what she needed a vacation from. But anyway, I was grateful for a getaway as well. We trekked through the maze of a property to get to our villa that we’d be sharing for the next few days. Obviously I shouldn’t be thinking of this, but when I used to stalk Brendan and his ex-wife on Instagram, they would always stay at places like this — places I could never imagine staying. Like a private villa steps from the beach with so many amenities we wouldn’t even have time to take advantage of them all. Like, it came with a private chef, a masseuse and a sauna.

We got to our room where Brendan immediately unpacked because he’s the kind of person who unpacks his bags completely before starting his vacation. Absolutely cannot relate. I sat my luggage down, pulled out fists and fists full of bikinis and dug through the pile until I found a matching one I liked. Time management + priorities.

Miguel and Jasmine met us down at the pool and they let us know that they’d already requested alcohol from the chef.

“I would kill to have your boobs,” Jasmine said to me.

I’m like excuse me, I would kill to have your entire body. Her modeling career may be questionable, but she sure has the body of a supermodel. But I appreciated her saying that because recently I’ve been seriously considering getting my boobs done. I’ve always had boobs too big for my body, but it was fine because they were really nice at least. But after turning 30, having a baby and losing weight, they just aren’t the same as they used to be. So I’d like to go in and have them wrangled back up to my chin to restore my youth.

I’ve always gotten the feeling that there is something…off about Miguel and Jasmine’s relationship. It’s weird. Miguel is always talking about how much he loves Jasmine and says stuff like, “Hold on, I need to check in with my baby,” while we are at happy hour. Then they’ll be all mushy gushy on the phone and he promises he’s behaving. And then he blatantly doesn’t behave and starts chatting up random girls at whatever bar we’re at. Miguel is first and foremost, very hot, but he’s also really flirty and makes super sexual eye contact. Even with me so I figured it was harmless. This one time, he attracted some young hottie to our high top and I watched him sweet talk her until she was practically salivating. And at this point he had an arm around her waist like he owned her. So according to girl code, I should’ve immediately gone back to Jasmine and let her know exactly what I witnessed and provided receipts and evidence. But Jasmine does the same thing. There’s her gross drug dealers who she loves to meet up with while we are out. I’m convinced she is sleeping with one of them by the way they interact — how they look at each other and how he feels comfortable touching her wherever he wants. The way Miguel and Jasmine talk about each other is kind of weird too. They talk about each other like they are reading from a script or they preplanned what they want to say about each other to other people. And Jasmine never complains about Miguel which is just unheard of. I’m sure there is plenty to complain about! So I’m like, you know what, I’m going to mind my business for once. I didn’t even talk to Brendan about it and assumed that they have some sort of open relationship or something.

So anyway, we all got in a cabana with our margaritas and I watched as Jasmine laid back and splayed her legs open like she was giving birth and Miguel crawled between her legs and rested his head on her stomach. I’m like, this is weird, trying to have a conversation with Miguel with Jasmine’s boobs on his head. During this trip, I also realized that they’re the kind of couple who needs to be touching each other and loved up at all time — even if it’s uncomfortable — which I love for them and hate for me. We sat around all afternoon and drank before dinner at a restaurant on the property. Miguel and Jasmine talked a little bit about their upcoming wedding (November in Puerto Rico), but neither of them are helping plan it and are mostly just excited for a Puerto Rico trip and for it to be over.

“And once the wedding is over, you can put a baby in here,” Jasmine cooed, rubbing the side of Miguel’s face.

First of all, ew. But another thing that is weird about their relationship and really bothers me about Jasmine, is that she is always doing this performative having-a-baby talk in front of Miguel/other people, but she’s told me on numerous occasions that she doesn’t really want kids. She will ask me specific questions about being pregnant and giving birth and then when I answer them she acts overly horrified and disgusted and swears she’s definitely never having a baby. And I completely get being apprehensive about it and everything — having a baby is a big life change — but then she’s always going out of her way to bring up how excited she is to get pregnant to Miguel while they are in front of people. Just don’t say anything at all! I guess it just reminds me of Brendan’s ex-wife lying about being off birth control and it feels deceitful.

We went back upstairs to get dressed and freshen up for dinner. Jasmine came to our bathroom to get ready with me and said, “Ugh, I need an Adderall before dinner. Do you need one?”

“Uh, no,” I said. One thing I will never do is take prescription medication without a prescription. It’s just so not me!

So she called Miguel to bring Adderall to her. They did this all throughout the vacation — popping Adderall like mints. Brendan and I were like, uh no thanks, we don’t need Adderall to function while on vacation. No offense.

The next morning, Brendan and I woke up bright and early to FaceTime Winnie, who was sitting on the couch with unbrushed hair eating dried mango. I gave her a little mini tour of our suite in the villa, but mostly wanted to show her the view from the balcony which overlooked the pool and the ocean.

“Oooo,” Winnie murmured, impressed, which I loved because I had a beach vacation planned for us the following long weekend.

After we hung up with Winnie, Brendan and I headed back down to the pool. Honestly it was nice to have a little alone time after spending the day with Miguel and Jasmine the day before. They were a lot. And alone time just meant Brendan telling me how “incredibly hot” I looked in my swimsuit so maybe that’s all I needed.

Eventually Miguel came down to the pool without Jasmine, who he said couldn’t get out of bed. Brendan and Miguel got to talking about work and mentioned how Gigi had recommended her sister for a role at the company. Gigi works closely with Miguel and she does a good job communicating and actually finishing things, but hiring her sister? Isn’t that some sort of HR violation?

“I feel like that’s a bad idea,” I said.

Miguel was like, “What? But Gigi does such amazing work, we definitely need two of her.”

Of course he made it sound sexual. I’m like, “Okay do whatever you want, but don’t be surprised if this blows up in your face.”

The wedding was later that night at a nearby resort. I don’t know what’s wrong with me, but I always cry at weddings, no matter who the bride and groom is. I just love love, I guess! I also cry about everything.

The reception was outside under a tent with string lights and lanterns and pampas grass everywhere. It would’ve been chic if it weren’t so fucking hot! After dinner, I didn’t even want to dance and I always dance. The drinks were good at least so that kept me going. I enjoyed meeting Brendan’s college friends who are exactly how you’d expect: slightly fratty with fancy haircuts, exposed ankles, Gucci everything. They were all perfectly pleasant and didn’t treat me like a mistress bimbo (or whatever Lala and Raquel/Rachel called each other) which is always my biggest fear. I’m literally not, but you know how people are.

I let Brendan mingle with his friends and sat down with Miguel and Jasmine. There were a zillion empty chairs but Jasmine was sitting on Miguel’s lap and playing with his hair so you know I was annoyed by that. By this point we were all a little bit sloshed and loosey goosey from all the drinks.

“Ugh, I just want to get into some trouble while on vacation,” Jasmine was pouting.

“By doing what?” I wanted to know. Y’all know I love to get in trouble, especially at someone else’s wedding!

Jasmine explained that there was a girl dancing behind me (“Do not turn around and look!”) who was the ex of someone’s friend or something and she and Miguel had always been attracted to her so they wanted to know if she wanted to spend the night with them.

“I think it might be weird,” Miguel said.

I immediately spun around to find a cute little brunette dancing alone with a glass of champagne. Queen. I’m like, OH. They’re that couple. The “we saw you from across the bar and really dig your vibe” couple. That made total sense to me.

“Oh my gawddd, who cares? Just ask!” I blabbed.

“I know, that’s what I said!” Jasmine said then turned to Miguel and started baby-talking. “I promise I won’t be weird about it, baby.”

“I’m mostly just offended that no one asked me to spend the night with them,” I said, kind of joking but kind of not.

Miguel turned to me with a serious look. “You’re not my type.”

Oh? Excuse me? What was that supposed to mean? What about me is not his type? I’m everyone’s type!

“Do you really think Brendan would let you stay the night with us?” Jasmine teased, to deflect.

It’s like, of course he wouldn’t allow me to have a threesome with his hot employee and his fiancé — that would be absurd! Which makes the “not my type” comment that much more unnecessary. I was so offended.

The next morning, Brendan and I woke up in bed and he started pushing his boner against me, you know, trying to get some.

“OH MY GOD,” I exclaimed, suddenly remembering. I turned around to face him and said, “Did you know Miguel and Jasmine are swingers?”

Brendan then started dying laughing, for no apparent reason that I could understand. He was laughing like this was truly the most hilarious thing he’d ever heard. I know I’m funny but this was a lot. I’m like, no seriously they are and they tried to recruit a cute drunk girl last night and she might even be here at the villa!

“Yeah, I know,” Brendan said once he’d calmed down. “I think they’ve always been fairly open.”

While all of this was adding up and explained everything, I don’t understand how it didn’t come up sooner. Jasmine never mentioned it to me? Not that it’s a big deal and it doesn’t even matter, but it caught me off guard. And maybe I’m thinking too much into this, but why is Miguel always flirting with me and eye fucking me if I’m nOt HiS tYpE? He’s not exactly my type either, but you don’t see me broadcasting it everywhere.

Winnie came home after a weekend with Brady and casually let me know that she’d hung out with Kara all weekend and that “Daddy kissed her.”

Oh? Baby girl loves to come home with a bit of gossip. And this was just a few weeks after I even found out about Kara’s existence so I was a little surprised that Brady brought her around so quickly. And was kissing her? I hardly even kiss Brendan in front of Winnie because it’s kind of…weird? I don’t know.

“Oh really? What’s she like?” I asked.

“Stinky,” my child answered.

“Winnie,” I said disapprovingly. Her new favorite way to describe anything and everything is “stinky” and I’ve lectured her about how it’s not nice.

Winnie smirked mischievously. She clarified that Kara had a dog that she brought and the dog was stinky.

“Okay. Did you like her?” I asked.

“No,” Winnie said back automatically.

You know Winnie. She likes to say no just for the hell of it so I wasn’t exactly shocked.

“Really? Why not?” I asked.

She shrugged and made a face.

“Was she mean to you?” I went on.

“No,” Winnie said.

“She was nice to you?” 

She nodded reluctantly like she was hoping to have a more juicy answer for me. I then asked her the only other thing I needed to know and that was what does this Kara person look like. Winnie described her as “very pretty” and “big and tall” with “beautiful hair.” Lovely. She also told me how Kara danced with her and made a video (Winnie recently started dance). It all sounded perfectly pleasant to me so that was a relief I guess. But I still messaged Brady about it — just to make sure. And because I am messy.

“Aww, Winnie said Kara’s dog is cute, but stinky,” I texted.

The “cute” part was added by me for a bit of pizazz because Winnie certainly didn’t call the dog cute. 

Brady replied with a photo of my child with a death grip on a wiener dog and a look on her face like this was all happening entirely against her will. She’s so hilarious and cute. And Winnie loves dogs so maybe the dog truly is stinky.

Anyway, despite how it all came about, I was excited to spend time with Brendan in Chicago. He’d taken a lot of trips to Chicago during college, he told me, because he and his friends liked to party there. Do college students typically travel to Chicago to party? Interesting. I hadn’t heard of that.

We were all going to Chicago for a conference and you know Mike, he (and his assistant) had planned the trip down to the minute with meet and greets and appointments and showings. But at least he had meals planned in though because Mike is typically fueled off black coffee and cocaine. Totally joking about the cocaine, I think. I was like, yeah, all of that sounds great, but I will need a night free because I must take my boyfriend to a Chicago steakhouse and don’t even bother booking a hotel room for me because I’ll be staying with Brendan, who travels in luxury by default. Like, if the penthouse suite or a first class seat is available, my man is going to scoop it up. I love that about him.

Mike and I had seats next to each other on the flight to Chicago and as soon as we sat down he started bitching about Paige and her “decision” to get pregnant, which he took as a personal affront. And who knows, maybe it was. They did supposedly have that little “flirting fling” or whatever. It’s been sort of assumed that I would cover for Paige while she is on maternity leave so she’s been slowly handing things (back) off to me. It’s a lot of work though so Mike should know that I will not be doing it for free.

When we landed, we dropped our bags off at the hotel and then walked down to the conference venue where Brendan would be meeting us later. I wore wide leg trouser pants, a tee from Aritzia with a headband by Lele Sadoughi and Gucci sneakers because I may seem like it, but I’m not insane.

Mike had a bunch of private meetings set up and I was prepared to let Mike do all of the talking and I would just look pretty and chime in when needed. But then Mike actually expected me to participate which was unfortunate because I didn’t have anything specific prepared. Oh well. If there’s one thing I can do, it’s bullshit. Y’all know me.

Eventually we met Brendan down on the main level of the venue and he looked so cute wearing his official conference lanyard (mine was tucked away in my back pocket like a normal person). I wanted to squeal and hug him because I couldn’t believe he was actually here, but I had to keep my cool since Mike was right there. We walked around the various booths for a few hours and discussed work stuff. Sometimes I feel like the third wheel with Brendan and Mike because they are really close and I wondered what it would have been like if Paige wasn’t pregnant and was on the trip instead of me.

After a while, we ended up parked in the middle of the packed conference trying to decide on our next move. Mike had arranged a welcome dinner later that evening that my old boss, Scott was invited to so I knew he would be around but didn’t expect to see him until dinner. But then the crowd parted and I saw Scott making a beeline for us with his arms spread wide like he expected hugs and cheers. He must be in his mid-40s by now and he looked good with his now completely bald head and trimmed facial hair. Scott has never really been my type, but there’s something sort of charming about him. Well, besides the way he used to turn into a complete pussy around Mike. It was such a turn off to watch him cower at a man who is a head shorter than him. Scott’s wedding ring shimmered in the light as he approached.

“Hey,” Brendan said next to me. “I’m gonna run to the bathroom.”

“Oh. K,” I said. Odd of him to scamper off right before he could meet Scott, but cool. Whatever.

Scott made a big scene greeting me and gave me an over the top hug so maybe it was good that Brendan wasn’t there to witness it. He was like, “So glad you’re here! I have all these ideas to run by you. Can you squeeze me in tomorrow?”

“For sure,” I said smiling and Mike gave me a raised eyebrow look since we both knew we had a full day of plans and meetings scheduled.

Eventually Brendan wandered back over and we all chatted for a while. Super casual small talk. I absolutely hate when people have in depth discussions about the weather.

I’m like, “Yeah, it’s gonna rain, but let’s talk about your family, Scott, are you still on Wife #1 or have you remarried?”

I totally didn’t say that, but I wanted to. Instead I talked their ears off about everything we’d seen so far. I could tell by the way he was watching me that Scott was dying to get me alone to speak to me. He probably just wanted to complain about his wife like old times, you know ol’ Scott.

At around 5, we decided to go to the rooftop bar at our hotel — per Scott’s suggestion.

“You haven’t been up to the roof yet? It’s the best view in all of Chicago!” he exclaimed at us and it’s like, when would we have time to hit up the bar, dude?

So anyway, we headed up to the bar and I took the initiative to order martinis for everyone. It just seemed appropriate. We mostly just stood around commenting on the view and the places nearby, like the new seafood restaurant that was a “must try!” according to Scott.

“It wasn’t around when you lived here, Reese, but you’d love sitting at the bar there. Great people watching,” Scott said and winked.

We used to hit up the bars near our office together and people watch so he was referring back to that.

“Ohhh,” I said, sipping my drink.

A little while later, Scott had struck up a conversation with Brendan about Brendan’s company. Normal stuff where he was recommending “leaders in sustainability” and Mike and I chimed in a few times. Then Scott started asking him questions about his company size and the biggest projects they’ve ever done and giving unsolicited advice and pointers. I don’t know, to me it felt like Scott was grilling him and since Brendan is trying to take a step back from his company he probably didn’t want to be talking about any of this anyway.

“Why does any of this matter? It’s not like you’ll ever be doing business together,” I said.

“Whoa whoa whoa,” Scott said, a bit too loudly. “I’m just making conversation, what’s so bad about that?”

And then he looked around like, “Can you believe this broad? She’s so silly!”

Brendan smiled apologetically at me and I think everyone was slightly uncomfortable after that. Oh well! Anywho, we had some time to kill before dinner so we all went to change and freshen up. Scott texted me asking to hit up the seafood bar after dinner. Of course. He’d planted the seed earlier and now he wanted to enjoy the fruits of his labor. He’s so transparent! I said maybe, I’d need to see how I felt after dinner because it had been a long travel day, etc. I thought if I said no then it would make it more awkward, you know?

Brendan and I walked back to the conference venue where the dinner was being held. He was pointing out places he used to go to, little hidden gems like the burger spot under Michigan Avenue and the old school pub in the financial district. Places I’ve certainly never been. I was like, “Well, tomorrow night I made reservations for us to have dinner at the restaurant I used to go to during my sugar baby era!”

We got to dinner where about ten people including Mike already were. A bunch of industry people who I’ve met on occasion. Brendan went to sit down at the table while I said hi to people I know and then I went to join him, but Scott intercepted me and took the seat I was going to sit in. So he was between Brendan and me.

“How’s being back in the city? Do you miss us enough to move back?” he asked all enthusiastically.

“No,” I said plainly and sat in the seat next to him. Up until the there was no way for him to know Brendan and I are a thing (unless big mouth Mike told him, of course) and he was laying it on a little thick. It was embarrassing.

“Oh, what a shame. Have you considered—”

Whatever. I tuned him out and started talking to the woman next to me. She’s some lady Mike has “done business with.”

“Aww, isn’t Mike the best to do business with?” I said in the most sarcastic way possible.

I didn’t realize that Scott and Brendan were having a conversation on the other side of me until I heard Brendan say something like, “Well, we are dating.”

Oh?

I spun around and Brendan gave me a look like he’d been caught. Aww, were they talking about me? Scott appeared to understand and changed the subject to deep dish pizza. He backed off after that, like completely backed off. He didn’t even press me about the seafood bar drinks. Look at Scott learning boundaries! All because of whatever Brendan said? If so, I was obsessed with that. The next day Scott didn’t even hang out with us and only waved at me while he walked past on a call on his AirPods. Oh well!

That night, Brendan and I ditched Mike and had a lovely dinner at RPM. We ordered a caprese salad, oysters, hamachi crudo, a big fat juicy steak and a bottle of wine. We hadn’t fully discussed the Scott situation, but Brendan called Scott a “creep” in passing conversation. And he’s definitely not wrong, but it made me slightly embarrassed to have gotten caught up with that creep previously.

After dinner, Brendan called an Uber to take us a few blocks to a place he used to go to to see if it was still there. He hopped in and said the cross streets like we were back in Manhattan in a yellow cab. I love him literally so much. Brendan’s beige flag is that he loves chatting up an Uber driver. Not the small-talk-weather bullshit that I despise, but he always uses the Uber Comfort selection or whatever so then he gets in and looks around and says, “Oh, is this new Tesla?” And they end up talking about cars the entire ride. Cute, but so annoying.

We ended up down an alley and behind a garage door at an underground speakeasy kind of situation. The kind of place where you need a password to get in. Or in Brendan’s case: a precious smile and a polite, “There’s two us?”

“This is sort of chic,” I said as we settled into a booth.

“Right?” Brendan said.

It really wasn’t, but that was fine. It was “stinky” in Winnie’s words and quite small and dingy. I figured we’d just have a couple drinks and chat but then a burlesque show started. One with really elaborate outfits and live singing. Huh? Brendan seemed proud of my shocked reaction as he could probably tell I was underwhelmed thus far. So it turned out to be really cool.

I had this idea in my head that Chicago is associated with Brady since I chased him all around that city and because of that, I thought it might become hard to visit. But honestly, I didn’t think about Brady once the entire trip. Not that I think about him normally, but I thought traipsing around our old stomping ground might dredge up some old memories or something. But nope! It almost felt like I was discovering the city for the first time again. I don’t know, it was just a really good trip with Brendan.

So anyway. I want to get back to posting regularly here again — which is insane since Paige just had her baby and I have much more on my plate. But I used to love getting all of my thoughts and feelings out and it was so therapeutic for me. A lot of my old posts are so hard for me to go back and read because my relationships were toxic, but I feel really happy now and I want to document that too. Also, I deleted my Twitter which is where I would typically go to announce new posts. So feel free to follow along via email to be notified of my new posts. To come: Brendan finally met my crazy parents and I can’t wait to tell y’all about that! Bye!

The next morning we woke up at like 4:30 since we’d gone to bed so early. I’d barely gotten any sleep because I was up thinking of how to articulate why I was upset about Brady’s girlfriend. Plus, I really needed to redeem myself after my low blow. Brendan sometimes describes his ex-wife as “mean” and I really cannot have him thinking I am too.

“Morning,” Brendan said, squeezing me. “Wanna go to the gym with me?”

It’s like, first of all, no. And secondly, we still needed to finish our fight from the day before.

“I would rather die,” I said.

He laughed and squeezed me tighter. “I love you. I’m sorry about yesterday.”

See what I mean? Why was he apologizing to me when I was the one who was out of line? He’s like impossible to fight with.

“Yeah, I wanted to talk about that,” I said. “I know you think I’m a lunatic so I feel like I should explain.”

“Mmhm,” Brendan said, not even denying thinking I’m a lunatic.

“It’s not about him having a girlfriend, I don’t care about that. I’m just concerned about Winnie and the effect this will have on her…” I realized that I probably still sounded bitter as I explained how I wasn’t sure if Brady’s new girlfriend would last as he is deathly afraid of commitment.

Brendan said that he totally understood where I was coming from and he didn’t want me to think he didn’t. And since he comes from divorced parents, he talked me through it and helped me think about it rationally. I guess I felt a little better, but he said that Margot is the only woman his dad ever introduced him to so if Brady brings Kara around Winnie then he better marry her.

Speaking of Winnie, a little while later, I heard the faint sounds of her getting up and padding through the apartment. Our routine in the morning goes like this: Winnie wakes up between 5 and 5:30, “sneaks” into my room to snuggle in bed with me and then she will dramatically talk about how hungry she is so we have to get up to have breakfast. Sure enough, seconds later I felt her tiny little arms around me. It feels like a long time coming, but Winnie is actually obsessed with me now. I don’t know how to explain it but I felt like she always used to just tolerate me, but loved Brady. But now she never wants to leave my side and tells me she loves me all the time and snuggles with me in the morning. And maybe that’s why I was so concerned about the potential of a new woman in her life. I only just got her to like me!

We all stayed in bed for a while and Winnie asked Brendan to make her exactly four waffles and eight sausages. I love how close Brendan and Winnie are and how seamlessly he fits into our lives. And it occurred to me that I was being kind of selfish by not hoping for the same thing on Brady’s side. If Winnie ended up loving Kara, that would be the best case scenario right? I needed to get over myself.

A few weeks later, I was minding my own business on Zillow, flipping through pictures of houses I can’t afford. It’s a hobby of mine. I like to bookmark my faves and then watch as the prices inevitably start dropping after a while. I was shocked and confused when I stumbled upon the listing for Brady’s house though. You know, the house he insisted he bought for Winnie to grow up in? It popped up since I’d saved it previously. Wait, what? It’s Brady’s house that he purchased solely in his name and he’s entitled to do whatever he wants, but I assumed it was a mistake (seems like a crazy big mistake to me). I took a screenshot and sent it to Brady.

“Yep,” he replied.

“What? Why wouldn’t you tell me?” I said back.

“I told Winnie. I figured she might tell you,” Brady said.

Winnie does have a big mouth, to be fair. For example, she told Brady how I cried about him having a girlfriend at dinner (thanks, Winnie!) and he was forced to tell her about Kara even though he hadn’t planned on it yet. So I guess I was kind of surprised that she didn’t tell me.

“Why are you selling? Where are you moving to?” I asked.

Brady gave me some vague explanation about how he wanted to downsize and it was a good market to sell. He avoided my question about where he was moving to so I asked again.

“I’m staying in Connecticut,” he said.

I wondered if this had anything to do with his new girlfriend and even if they were moving in together (which would be absurd). It all seemed like a lot of change for Brady — who notoriously never changes anything about his life. Not even his hair. But perhaps change would be good for the guy. The biggest memories I have in that house are escaping the pandemic, slowly breaking up with Brady and then being majorly depressed so I guess I can’t really blame him for wanting to get rid of it.

And speaking of moving in together, Brendan’s new apartment is finally complete. It was really fun to watch it all come together, especially since I had a hand in picking every little detail from the bathroom marble to the pots for the indoor plants. And he invited me to check in on the progress whenever he went to see it because he knows I have an eye for detail and if there was anything out of place, I was going to find it. The cutie construction team started calling me “The Boss.” So maybe this is absolutely insane, but I thought he might ask us to move into his new apartment with him. Especially since I kept dropping hints — by claiming closet space for my bags and picking out a paint color for Winnie’s room. And half of the hardwood in the primary would be without underfloor heating if it weren’t for me! And I kept bringing up the fact that I was looking at new apartments on StreetEasy to try to get him to bite. But nope. I moved into my new apartment and he moved into his and it’s fine. It’s too soon I guess and we spend almost every night together anyway.

Mike had a trip to Chicago planned and since Paige is super pregnant, he asked me to go with him instead. I wasn’t particularly excited to travel with Mike, but a Chicago trip sounded fun. And then I had the bright idea to invite Brendan and we could make a whole thing of it! I’d show him around all of my old haunts and the places I used to act a fool at!

Brendan was like, “Hmm, I don’t know if I’d want to do a middle of the week trip. Maybe another time or something, idk.” All indecisively. And it really bothered me because why wouldn’t he be dying to go to Chicago with me? Why did it matter if it was in the middle of the week if he’s working less at his company? I was even more mad a few days later, when he told me that Mike said he should come to Chicago “for networking” and so now he was coming on the trip. Not because he wanted to spend any time with me or see where I lived, but because Mike asked him to. I guess I can understand him not inviting me and my three year old to live with him in his sparkly new house, but that paired with him not wanting to take a trip with me made me think maybe our relationship isn’t as serious as I thought. Like he’s not as into me as I’m into him. I realize that I’m with his family at most of their holiday events and trips, but still. He doesn’t exactly have to go out of his way to include me in that.