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!