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!