Mike sent me to Chicago for a conference all by my lonesome in June. I’m sure Mike loves that he can trust me to do things on my own and actually get stuff done. Paige was always pretty good at talking, but rarely moved the needle in regards to…really anything. I wonder how she’s doing.

So anyway, Mike said he was too busy to go to Chicago so he asked me to go instead and gave me a list of things he wanted done while I was there. All of it seemed extremely doable, but on my way out of his office he said, “And take Scott to dinner too, please. It’ll be my treat.”

I’m like, uh?? Mike is so clueless when it comes to interpersonal relationships — on what planet would I take Scott to dinner? If anything, he should be taking me to dinner, but I had no plans of seeing that man while I was in Chicago.

Brendan also decided that he was too busy to make the trip so he sent Miguel instead. And since Miguel can’t do anything on his own, Gigi came with him. And since Gigi was coming, Izzy was coming too.

My parents flew in to stay in my apartment and take care of Winnie since I was going to be in Chicago for 4 days. I thought it was an excellent idea and since they were offering, I would definitely take them up on it. Did I tell y’all that my dad is retiring next year? So they’ve been discussing what they want to do after he retires and where they want to retire to. My dad has ideas like South Carolina or San Diego, but my mother seems to think New York would be a nice, relaxing place for them to move to. It just doesn’t seem realistic to me and I can’t imagine them (her) living so close. I haven’t lived near my mother in 10+ years and while it would be nice to have them around for babysitting purposes, I can’t imagine it would be worth it. As y’all know, boundaries are non-existent to my mother and she would completely exploit our living arrangements in the worst way.

So anyway, I flew to Chicago on Sunday afternoon for the welcome networking event. I wasn’t particularly enthused about going since none of my friends would be there, but there was going to be an open bar and that was enough for me. Plus I knew it was going to be filled with girls and gays so I was looking forward to a night of gossiping and gabbing.

My mom sent non-stop texts, videos and pictures documenting their stay. By Sunday night, she’d already taken it upon herself to deep clean the kitchen and fill it with food (Winnie and I don’t typically keep much food in the home) and go through the apartment to find enough clothing for a single load of laundry which she strung all over the house to dry since she wasn’t sure if I wanted them in the dryer. It was all a lot and I was so glad to be missing that.

Monday was busy with presentations, panels, workshops, a luncheon, etc. In the evening, I met up with Miguel, Gigi and Izzy for drinks near the hotel. I hadn’t seen them at all during the day at the conference which I later found out was because they skipped most of it. Just wait until Brendan found out about this! The bar we went to was near deserted and Gigi and Izzy started in on their incessant squawking like they do — really giving the city pigeons outside a run for their money. They were up running in circles around the bar while Miguel and I sat there talking like adults. He wanted to talk about baseball and the Cubs and since I’ve been to a Cubs game or two I pretended to know what I was talking about.

I’m like, “My ex was obsessed with the Cubs so he dragged me to the games with him sometimes. Have I told you about my ex, Brady? He’s my baby daddy?”

Obviously I’d mentioned Brady on an occasion or two to Miguel, but he’s polite and said no so I could explain my backstory over lots of drinks.

“First I have to tell you about Carly. She’s the whitest person I know. She’s from Rockford,” I said.

“Makes sense,” Miguel said.

I went into very graphic detail about the beginning and middle of me and Brady’s relationship and Miguel listened and interjected at the right parts.

“No offense,” he said at one point, while I was in the middle of an animated story about a night out. “But he sounds like a fucking dick. I don’t get the vibe that he was that into you.”

“Well, I get that now! Obviously!” I screamed. What did I say about Miguel being polite? I take that back.

“But it doesn’t sound like you were that into him either,” he backtracked.

“No, I was totally in love with him,” I clarified.

Then Miguel started telling me insane stories that made everything I’d previously said seem really sane and not out of the ordinary in the slightest. Miguel has apparently lived 14 lives. He’s like, “I got held at gunpoint because I was somewhere I wasn’t supposed to be in Colombia, but on that same trip I had a sexual encounter with two sex workers so it was worth it!”

“This place is wack,” Izzy said abruptly. “Chicago sucks. Is there anywhere else we could go, Reese?”

“I mean, it’s Monday night,” I said, offended on behalf of my beloved city. And I was kind of loving the lowkey quiet vibes of the empty bar. Did these bitches think we were in Vegas or something? What were they expecting?

But still, I was not about to let them slander Chicago without getting the full experience. Uncultured little twats. So I called an Uber to take us to a hotel bar that I know gets rowdy and plays hip hop and R&B music. It was filled with tall, but ugly men so Gigi and Izzy were satisfied. Miguel and I squeezed into some seats at the bar together so we could continue talking.

I’m like, “I used to come here with my old boss. We had a little fling or whatever before I found out his wife was pregnant.”

“His wife? I feel like I missed a chapter,” Miguel said.

So I filled him in entirely on the backstory and basically gave him a speedrun of my career journey. At the end, he said something like, “Ah, you like ‘em married. It all makes sense then.”

What the fuck was that supposed to mean? I know he wasn’t insinuating that I got with Brendan while he was married and that’s why it all made sense. Brendan may have been married when we first met, but we didn’t get together until after he was divorced. And anyway, the last year or so of his marriage doesn’t even count if you ask me since it was borderline abusive on her part. Brendan sometimes lets it slip just how toxic their relationship ended. Apparently she made him cry once (you know he’s sensitive) and threatened physical harm. Insane considering she’s like 99 pounds and Brendan has all that trauma around his mom abusing his dad. It’s actually really upsetting to hear about it. So whatever Miguel was trying to say was completely not valid!

Eventually it was getting late and I told Miguel I was leaving.

“I’m gonna stay and make sure these two get home safely,” he said, gesturing to the bird sisters who were hounding a group of men at the other end of the bar. “Let’s get dinner tomorrow without the girls.”

“For sure!” I said and then got the fuck up out of there.

I had some missed calls and texts from Brendan, but I first wanted to call my mother to make sure everything was going well and Winnie got to sleep okay. One thing about Winnie — she will stay up all night if you let her.

“Hi sweetie,” my mom answered, with glee and enthusiasm despite the fact that it was after midnight New York time. “Winnie just got to sleep.”

“Just?” I repeated. “She’s usually in bed before 9.”

“Well, we were distracted and having fun. Brendan stopped by…” she said.

“What?” I screamed. “Why?!”

“He was just checking in. Is that a problem? He has manners. He stayed for dinner,” my mother continued.

“Oh my god and what did you say to him?” I said, trying not to go into full panic.

“What do you mean? We all talked and ate. He’s got a good head on his shoulders. He’s very nice.”

“Obviously!” I love how it had taken her this long to realize it. “I just don’t understand why he came over when I’m not there.”

“I guess he just wanted to see me and your dad. And Winnie too. She loves him, you know. If you decide to marry him someday, I think he will be a great father figure for when Brady isn’t around.”

“Well, I hope you didn’t scare him away,” I said bitchily.

“I didn’t,” she said back, equally bitchy. “I don’t understand what the big deal is and why you’re always trying to hide him from us.”

I was not about to argue with her and explain that actually I was hiding them from him because my mom is unpredictable and lacks boundaries and self awareness like I mentioned before, I have no idea where she is with her sobriety journey and when she gets drunk it is embarrassing and she has no filter and I didn’t want her to say something offensive to Brendan who is a very sensitive Pisces.

So we hung up and I called Brendan.

“Hey,” he answered affectionately and I just wished he was with me because I missed him and I wanted to squeeze him.

“I didn’t know you were going to my apartment,” I said.

“I know. I just stopped by to say hi on my way home. Sorry, I tried calling you,” he explained.

“And you stayed for dinner?” I asked, horrified.

“Well, your mom invited me to. She ordered Greek food.”

Of course she did! I made him tell me everything that happened from the moment he walked in the door and he went into detail like I like (“Your mom had glasses on, I don’t think I’ve seen her in glasses”) and probably sugar coated everything because it all sounded quite tame and normal.

At the end I said, “Okay, thanks for stopping by to say hi. I think my mom appreciated it, but you don’t have to bother doing that again.”

“Okay,” Brendan said, sounding slightly defeated.

I felt bad so I tried to explain. “You know it’s not about you. I told you, my mom is an actual insane person and I don’t want you to be subjected to that.”

“She’s really not, but okay. Understood,” he said.

We continued chatting for a little bit after that and I told him about the day, who I met and hanging out with Miguel, Gigi and Izzy. Brendan said something like, “I’m glad Miguel is keeping you company,” because he knows things are strictly friendly and professional between Miguel and me. And it’s like, yeah, Miguel has to keep me company since you’re sOoOo busy.

The following day was more of the same shit, but in the middle of the day I got a text from Scott.

“Surprised I haven’t bumped into you yet — heard you’re in town. What about drinks or dinner later?”

Yeah fucking right!! I didn’t reply to him obviously. Later on, I went to a conference happy hour and then I met Miguel at Gilt Bar for dinner. I was feeling myself after having approximately 4 midori sours at happy hour and slid into the curved booth next to Miguel. He complained that Gigi had ditched him during the day at the conference and he saw on Instagram that she and Izzy were out hiking around the city and not doing any kind of work. Of course I lectured him about how the sisters were going to continue doing whatever the fuck they wanted because he and Brendan allow it and they face no consequences or accountability. It’s totally not my business how Brendan chooses to run his company and I hardly ever give my opinion, but I couldn’t help myself.

We ordered a bottle of wine to split and I ordered a bit of everything since it was Mike’s “treat.” Sure, I was technically supposed to treat Scott, but I don’t like Scott.

So Miguel has always had this flirty sort of vibe with not just me, but everyone. And you know how I can be, especially once I start drinking. So I guess the conversation was a little bit flirtier than normal. But kind of like, not. Miguel is very hot and attractive, but I’m good friends with his wife and he works for my boyfriend and I know too much about him so I almost don’t even see him that way anymore. We sat side by side and he kept one arm draped over the back of the booth behind me. We ate pasta and meatballs and burrata and Miguel made some comment about how I can actually eat and that Jasmine eats like a bird. Again, I take back any mention of him being polite. We basically spent the entire dinner talking about our respective partners, Europe, college, food and the Cubs. Jasmine even FaceTimed and we chatted with her for a bit.

Dinner definitely felt kind of intimate, but also not, because it’s just Miguel. We got espresso martinis after we ate and I was definitely drunk and just saying whatever the fuck I wanted.

Miguel said, “So how about after this, you come up to my room for a nightcap?”

I blurted out, “No!” and laughed because clearly he was joking.

“You sure?” he said and this delusional man was dead serious. Did he really think I was going to agree to that?!

“Yeah! I already drank way too much and I need to get some sleep,” I said.

What did he mean by “nightcap” anyway? Was that a euphemism for something else? For what reason should I be drinking with Miguel, alone, in his hotel room? And did this have anything to do with the “you like them married” comment?

“Lightweight,” he said playfully, but I could tell he was surprised by the fact that I hadn’t agreed to it.

After we paid, we went outside and Miguel told me his plans of getting one last drink elsewhere. I told him that I was going to walk back to the hotel (insane idea, it was late and dark and I was drunk) and he said that Brendan would kill him if he let me do that. So he hadn’t forgotten Brendan exists? So why was he asking me to go back to this hotel room with him? Would Brendan not kill him for that too?

So anyway, he waited with me for my Uber, hugged me goodbye and then I proceeded to have a very graphic, very sexual dream about him that night.