Photo-Illustration: James Gallagher
This week, a woman sleeping with the married bartender who works next door while trying not to spy on her ex across the street: 28, single, Brooklyn.
11 a.m. I wake up at my parents’ house in Connecticut. I get a text from the Bartender, like clockwork. “Good morning! Are you in town?” I’m not, but I will be later, I text him.
I live right next door to the bar where he works. We’ve always had flirtatious, but relatively harmless, banter. One night, years ago, when I was living in the room that shared a wall with the bar’s backyard, I heard two people having very loud sex outside my window. The next time I went into the bar, I told the bartender about it, but he claimed it wasn’t him, since he’s married. Only recently, years and years later, did he reveal that it was him. That’s when things started to escalate between us.
2 p.m. On the train heading back to the city, I sit next to my brother and his girlfriend. We don’t really talk, each of us absorbed in our own activity. I choose the crossword puzzle and put my headphones in.
5 p.m. Back in Brooklyn and all settled in, I get a text. “Here.” I wait for him to come up the elevator. When he walks in, we go straight to making out. We make our way into my room and immediately start rolling around in bed. Clothes come off, condom goes on, and he has his way with me for the next few minutes. I usually take control in the bedroom — I feel more empowered, and it tends to just feel better — but I enjoy having him boss me around, squeezing and pushing my body where he wants it to go.
After he finishes, he wastes no time with going down on me until I finish. He comes back up flushed and dripping in sweat and we lay there wrapped in each other’s arms for a little while. It almost feels normal.
“So … what is your situation, by the way?” I finally ask.
“What do you mean?”
He confirms with a nod.
“And you guys are not in an open relationship?”
“Oh, no. This is most definitely … illicit.”
He checks his phone. It’s his boss calling. He heads in for his shift and I get ready to go out with friends.
9 p.m. We’re having a couple drinks. They all know about the Bartender but it’s a judgement-free zone, which I appreciate. We call it a night pretty early.
10 a.m. I told myself I would re-download Hinge after the holiday, so here goes nothing.
My last real, serious relationship was with my college boyfriend and ended about five years ago. Since then, I’ve mostly been single and dating, with a few medium-term or semi-serious situationships peppered in. At this point, I’m not really even sure if I want a boyfriend!
12 p.m. I match with Michael and begin chatting. He seems … nice. Let’s see where this goes.
9 p.m. I’m in bed, but I don’t feel right. I think last night is starting to catch up with me. Before I descend into a fit of anxiety and dread, I FaceTime my best friend, Will, and we talk about our holiday plans and future ski-trip plans until I start to feel better. We hang up and I fall asleep.
9:30 a.m. I start the workday by taking my Monday morning meeting from my bed. I work at a small but growing start-up where I manage about 20 clients. My boss is out on vacation this week, and while I probably should use this time as an opportunity to get a bunch of things done so he comes back impressed, I take it as an opportunity to chill out. The meeting ends and I go make myself a short stack of pancakes.
3 p.m. I get a message from Michael on Hinge: Want to grab a drink tonight? The truth is I don’t. I’m still exhausted from the weekend and feeling the lingering anxiety from the other night. I decide to leave him hanging for a bit while I decide what I want to do.
5 p.m. Ready to close my laptop for the day, I move on to one of my favorite pastimes: flopping on my bed and staring out the window. And because I live on the fifth floor of an apartment in New York City, that means I’m faced with a view of … other people’s homes. My eyes scan the building across the street until they light on the Neighbor’s (dark) unit.
Let me tell you about the Neighbor. We met because I noticed how hot he was from my window and orchestrated a random “hello” down the street. From there, I saw him out at a bar one night and we started dating. It was just about this time last year that we stopped seeing each other. Or more accurately, it was just about this time last year that he canceled plans on me, only for me to then see that he had another girl over instead. I still remember the sting, and I can only equate it to feeling like you just got punched in the throat, sending you gasping for air but unable to catch a breath. Am I being overdramatic? Probably. My roommate’s home so I head out into the living room to talk about our days.
6 p.m. I’m spying again. The lights are on now and he’s home watching TV. The candle is burning. That means She is coming over. I don’t want to see this. I reach for my phone and text Michael from Hinge: I’m down! Where should we meet?
8 p.m. I make it to the bar first, but only by about 30 seconds. Michael walks in and I go up to greet him. I immediately realize we don’t really vibe. It’s not like there’s anything wrong with him. He’s a cute, smart, interesting guy, as I come to discover over the next two hours. He’s just not for me.
9 p.m. After my second glass of wine runs dry, I pause and tell him that I think I’m going to call it a night. He seems apathetic about that. I walk home listening to a mix of Taylor Swift and Destroyer.
10 a.m. It’s another day at work but I’ve also decided to wrap things up extra early for some self-care later on.
3:30 p.m. I close my laptop early and take the subway down to FiDi to see my chiropractor. After cracking every vertebra in my spine, the masseur comes in. I lay there while he digs into all of my knots, sporadically unleashing “ahhhhs” and “owwws” completely involuntarily. By the end I feel looser, straighter, and more relaxed.
5 p.m. I head uptown to see my therapist for our weekly session. I originally started seeing her a couple years ago after a series of debilitating panic attacks. Today, we talk about how I tend to like men who are unavailable, and I tend to be repulsed by men who want to date me. We agree that I’m scared of hurting men who want to date me.
7 p.m. I end the designated self-care day with a hot-yoga class at some bougie studio, sweating along with 20 strangers while the instructor plays SZA loudly over the speakers.
10 a.m. I’m cold in my apartment but I don’t want to turn the heat on because it’s too expensive. I settle for a pot of tea and drink that to warm myself from the inside out.
10:56 a.m. My phone buzzes and I have an unexpected text from a guy named Bryan whom I dated for a few weeks over the summer: “Popped into NY last minute. How are you?” I’m surprised to hear from him, since the last time we spoke I told him I didn’t feel a romantic connection with him and thought it’d be best if we stopped seeing each other.
1 p.m. I keep thinking about the text from Bryan. What does he want?
8:23 p.m. I have a long-overdue FaceTime date with one of my best friends who left the city during COVID. It’s great to catch up, but FaceTime will never replace in-person interaction and I miss her being here.
10:47 p.m. Another text from Bryan even though I still haven’t responded to the first one. “What’re you up to? Come grab a nightcap!” I toy with the idea. It could be nice to feel chased right now. Maybe we could even go to the Bartender’s bar and I could make him feel a little jealous … No! That’s a horrible idea — what if someone did that to me?
I tell Bryan it’s late and I don’t think it would be a good idea and go to sleep.
9 a.m. I get up to make coffee and realize my roommate used the last of the oat milk. Oh, well. To the bodega, we go! As I cross the street to the bodega, I spot The Neighbor on a jog, and we share a silent five-second eye contact.
9:21 a.m. Back in my apartment, I wonder what to do about the sighting. I decide to send him a text, the first in a year. “Wow, I legit did not recognize you there for a moment, otherwise I would’ve said hello.” I pretend to work while I wait for him to respond.
“Haha, I thought you were just glaring at me. Hope you’re doing well! I wasn’t sure if you’d moved away or not.” I wish I had the luxury of not knowing whether he’d moved away or not.
We go back and forth like this a bit, and he takes this casual conversation as an opportunity to say he’s sorry. “I know it ended badly and it was all my fault. I haven’t felt good about it and I want to apologize.” I don’t know if this constitutes “closure,” but it’s healing to have your feelings validated by the person who hurt you.
8 p.m. I go out for drinks with a group of girl friends. We talk about everything under the sun: friends of ours who have recently broken up, makeup, cults. There’s nothing special about tonight, but we drink and laugh all the same.
11 p.m. On my walk home I take a quick peek into the bar to see if the Bartender’s there. I don’t see him, but I don’t look very hard. Best to just go home anyway.
9:45 a.m. I’m hungover, but it could be worse.
3:30 p.m. I remember it’s The Bartender’s birthday today. He very deliberately told me this the last time I saw him, and also mentioned he’d be working at the bar that night. I debate whether to send him a text, stop by the bar later, or do nothing. For now I choose nothing.
8 p.m. Tonight a group of friends and I are doing Secret Santa, and I’m hosting. As people start trickling in, it’s unclear where this night is heading — a couple people arrive with a bottle of wine in hand, some with a couple six-packs, and finally Cam shows up with a bottle of tequila and a bag of coke. Choose your own adventure! Spoiler alert: We all choose Cam’s.
12 a.m. We make our way to one of my favorite bars, where you’re almost guaranteed to have a good time. Who doesn’t love an unpretentious bar where there’s never any line, and with good music and a bumping dance floor?
My friend Luke shows up. He and I have known each other since high school, and we share a special bond as a result. He’s always felt like a younger brother to me, probably since he was good friends with my younger brother growing up. Then again, he recently broke up with his girlfriend, so that may change things.
1:45 a.m. It’s getting late. I find Luke at the bar. As we chat, I notice his eyes move up and down my face, taking turns looking at my eyes and glancing at my lips. After it happens a few times, I decide to say something.
“Are you trying to decide if you want to kiss me right now?”
Luke throws his head back and laughs before nodding. “Uh yeah, I was kinda thinking about it …”
Fuck it — we lean in and start making out. This is so weird, I think, I’m making out with Luke. I pull back. Luke looks unsure if he did something wrong. I tell him everything’s good, but it’s late and I think we should probably call it a night. Separately. We kiss good-bye and I head out.
2:05 a.m. Technically, the bar is closed. But since it’s the Bartender’s birthday, I decide to stop by. There’s a few stragglers there. He sees me through the window and smiles, running up to the door to let me in.
“Happy birthday!” We hug. It’s weird to hug him in front of these other people who don’t know.
“Come hang for a bit!” I plop down on a stool at the bar, and the Bartender pours us both a shot of God knows what. We toss it back and chat over the bar for a few minutes.
“Are you around tomorrow?” We share a knowing look, like we are speaking a secret language.
“Yeah, I’ll be around.”
“Excellent. I’ll text you.”
We hug again and I finally head home.
Want to submit a sex diary? Email email@example.com and tell us a little about yourself (and read our submission terms here.)