Illustration: Marylu Herrera
Before we get to this week’s column, some news: Sex Diaries is becoming a book! Below, we’re happy to introduce the cover of Alyssa Shelasky’s More, Please: Real-Life Stories of Non-Monogamy and Polyamory, a compilation of never-before-seen diaries. It’s on sale July 14, but you can preorder More, Please from Random House now.
Photo: Courtesy of Random House
This week, a woman and her finance-bro friend with benefits have group sex two nights in a row: 29, single, NYC
DAY ONE
7 a.m. Wake up to a text from Tara. She’s down to meet tonight for drinks “to see where it goes” with Finn, a FWB I’ve been hooking up with for a few weeks. I know where it’ll go: straight to Finn’s apartment. Tara and I had good chemistry on our first date last week, and Finn is really hot, so she’ll be into him. Text Finn. He’s delighted. I’m a big fan of the group dynamic.
8 a.m. I have a whole day of anticipation ahead. First stop: the gym. Finn and I met online. He works in finance and has a “recovering bad boy” energy that I’m very into. The first night we went out, he got me off over and over, and we’ve beaten our record many times since. Our emotional connection is strong, too. I don’t know where it’s going to go, but I’d consider something more serious with him if the timing aligns.
2 p.m. The workday could not drag any slower. I advise very wealthy families on their philanthropic strategies. It can be fun, but not as fun as daydreaming about tonight.
5 p.m. Wrapping up. Planning my look. I’m going to wear red boots and curl my hair.
8 p.m. Quick call with Finn while I do my makeup. Tara is so hot. Also, she’s progressive and intelligent, both of which are critical for me. I only want the best of the best, which makes it harder for us to find people to hook up with, even though we’ve been on that mission since we met.
9 p.m. Meet Finn at the bar. He loves the outfit. Men are ultimately predictable, which means they’re not hard to please. Tara meets us shortly after and looks fantastic. She’s clearly nervous, but I’m great in my role as the bridge between the two. Finn and I are very extroverted.
10 p.m. Finn pays and we go to a sultrier bar. The best date move is a casual spot for drinks, then a dimly lit, speakeasy-esque joint. Tara seems attracted to Finn, which makes me happy. A lot of times when I hook up with couples, I meet the woman first, and she oversells the man’s appearance. You expect Jacob Elordi and are instead greeted by … not Jacob Elordi. It’s important to me that Tara gets what she wants out of this.
10:30 p.m. We attempt to hook up in the bathroom. A bartender yells, “Sorry, one at a time!” Why have a big bathroom if people can’t have threesomes? This city has gotten soft.
11 p.m. We go back to Finn’s. Tara is an active participant, takes direction, and is equally attentive to us. Very fun. Sometimes women have a clear preference, which can detract from the experience. Unless, of course, she prefers me.
4 a.m. Tara and I get Ubers. Damn, that was fun, but I’m exhausted.
DAY TWO
11 a.m. Finn and Tara both text about last night. They can’t wait to do it again. It’s easy for one person to feel left out, but our balance was great.
12 p.m. Therapy. A few months ago, I couldn’t even think about sex without freaking out. I have OCD, and for the past six months, I’ve gone hard at exposure therapy, which involves forcing myself to be exposed to triggers like sexual or “immoral” ideas and imagery. It’s rid me of my need to compulse almost entirely. (I don’t really think sex is immoral, but that’s OCD for ya.)
1:30 p.m. Finn texts. A girl we’ve been messaging with wants to hook up tonight. I’m beat after yesterday, plus therapy, plus work, but he sends a picture and she’s hot. I’m down if we do it early. I can’t be doing the 4 a.m. bedtime again.
4:30 p.m. Head to Finn’s. I prefer to meet women 1:1 for drinks first to feel out the vibe, then introduce them to him, but 2026 is my year of adventure, so I’m trying to be more spontaneous, and less of a stickler for optimized processes.
6 p.m. The girl is … interesting. The photos were generous, and I don’t think she has a bisexual bone in her body. I end up playing more of a supporting role, which is not my thing. Finn does a good job of trying to get her to engage with me, but there’s barely even an attempt on her part. I don’t want anyone to violate their boundaries, but she said she was down for us both …
7 p.m. Going home. Some people are into watching, but I’m not one of them. She says she’s going to stay, though Finn politely hints at having stuff to do. Whatever, good luck with that. Not to be the most type-A person alive, but this is why we stick to the process. There’s a very specific etiquette to threesomes and a formula that guarantees success, but men throw quality to the wind if it means instant gratification.
DAY THREE
6 a.m. Caffeinating like a madwoman as I get ready for the gym.
8:30 a.m. Arrive at the office, which is two blocks away from my gym in midtown. My office is right next to that of one of my best friends. I tell her all about my weekend of back-to-back threesomes.
12 p.m. I get a text from a couple I haven’t hooked up with yet. We’ve been working on it for a few weeks now. They spend a lot of time up north, and it’s been a busy season for me, but we’re both free tomorrow night. We make plans to meet at a bar.
6 p.m. Finally, I can go home. These days, I’m much more into my life outside work. I wasn’t able to have a social life for a long time because of my OCD, so I overcompensated and leaned the entire way into work. It paid off, but my current situation feels so new and exciting. I’m probably overdoing it, and I’m sure I’ll strike a balance eventually but, until then, may these wild oats continue to be sown with the 10s of New York City 🙏, amen.
8 p.m. Text the couple that I’m excited to see them and they both respond in kind. The woman sends a sexy pic. She’s so hot it’s stupid. I read my book, Empire of Pain, and fall asleep early.
DAY FOUR
6 a.m. Wake to a text from my sexy British man, Mr. Darcy. I met him on Feeld. He lives in London but travels to the city frequently for work. Hearing him talk in his little accent is incredibly hot. He’s much older and looks like Patrick Dempsey with longer hair.
9 a.m. Post-gym coffee and gossip with my best friend. I truly don’t know what I’d do without her. Sometimes I think about leaving this job, and someday I will, but not working next to your best friend sounds awful.
11:30 a.m. Mr. Darcy asks what I’m doing tonight. He loves hearing about my threesomes, at least while he’s across the pond. He’s unexpectedly sweet and has a lot of depth to him. He asks me about what I’m reading and says that books are like “a window into the soul.” I’d be rolling my eyes if he wasn’t so hot.
3 p.m. Ask Mr. Darcy if he’s ever heard of certain exclusive play parties in London and New York City. I got invited to join by another couple who are deep in the scene. Mr. Darcy and I each apply, and I get accepted right away. They have one coming up in London, but none scheduled in New York yet. We plan to keep an eye out so we can go together.
5 p.m. Leave work to get ready. This is what I love about sleeping with older people: You’re in, you’re out, and you’re in bed by 10 p.m. A steamy evening that ends in eight hours of sleep? Talk dirty to me.
7 p.m. At the bar to meet my couple. The woman is so hot, and crazy tall. I’m not as attracted to the man. That’s pretty standard for me, and he’s cool, so it’s fine.
8 p.m. After two drinks, we head to her huge, well-decorated apartment. She’s clearly wealthy. The sex is tame, but that isn’t necessarily bad. The man and I are in missionary with the woman playing a supporting role. Main character or not, she’s great. I love hooking up with older women. They’re much more confident than girls in their 20s.
10:30 p.m. Home, showered, cozy in bed. Tonight was fun, and I know they want to see me again. Not to brag.
DAY FIVE
8 a.m. Mr. Darcy asks about last night. One of my favorite parts of sleeping with couples is recalling the details for other men. He asks about the guy. I say he was sweet, which makes Mr. Darcy laugh. Apparently, men don’t want dates to describe them as sweet. That’s an oversight, since sweet is pretty much the best thing a man can be.
11 a.m. It’s shaping up to be a busy day with a lot of Zoom calls, which is fine, but exhausting.
12 p.m. Lunch with my best friend. We go to a small café for salads every day. I keep meaning to be better at meal prepping, but who wants to give up walk-and-friend time?
1 p.m. Mr. Darcy gets accepted into the club we applied to, thank god. I really want to go, but by myself. People in this scene are typically great about consent, boundaries, and communication, but it only takes one bad experience for everything to go down the drain.
3 p.m. Scrolling on Feeld on a break, even though my roster is too full as it is. Dating is just so fun, especially when you take the pressure off. People get so stressed out about finding the one. I want that too, but it’s just not that serious. Whether some man finds me hot, texts me back, wants to marry me… I mean, who cares?
6 p.m. Leaving work. Text Mr. Darcy a video describing my day for him to wake up to. I might be insane for giving this man the time of day beyond sex, but maybe not. He’ll be in town in two weeks, and I can’t wait to see where our chemistry goes.
7 p.m. My couple texts asking if I’m around next week. I tell them I’d love to see them. I typically see Finn on the weekends, and I know they’ll get me to bed at a reasonable hour during the workweek.
10 p.m. Fall asleep watching Modern Family.
DAY SIX
9 a.m. Wake up with a little sore throat. All my deep-throat queens know the struggle, but my OCD tells me it could be an STI. My brain likes to obsess over worst-case scenarios. I set a timer for two minutes and let myself compulsively Google STI symptoms until it goes off.
12 p.m. I’m able to work without obsessing, but I schedule an STI panel for this evening anyway. I figure it’s the responsible thing to do, though I know that’s just an excuse to give in to a compulsion. Two things can be true.
2 p.m. Mr. Darcy and I exchange videos about our days, and it turns spicy. I tell him I’m almost all the way through my archive of sexy pictures and videos of myself, and he says we can make more together. This man better be able to put his money where his mouth is when we meet for the first time come February.
7 p.m. Clean bill of health. I knew it, but if I’m going to be out in these streets, I want to be safe.
8 p.m. Make some new content for the archive. I love taking spicy pics. One of the best parts of my journey to Eat, Pray, Love across New York City has been how much more confident it’s made me.
9 p.m. I want to send pics to Tara, but she has the flu. I think literally everyone alive is sick right now. Thinking about the threesome we had with Finn turns me on even more, but I opt for “hope you’re feeling better!” To be an adult is to consider someone’s humanity despite being massively horny.
DAY SEVEN
9 a.m. A few of my roster folks texted after I went to bed, about plans for this weekend. I need to decide who I slot in and who I can push to next week, but that requires coffee.
10 a.m. What they don’t tell you about good, non-monogamous sex is how much coordination it requires.
1 p.m. By the time I leave for the gym, everyone’s gotten back to me and my dates have been set. I love coordinating with women because they can actually plan things in advance. Men love to “play things by ear”, but I’m a busy girl, and that doesn’t really work for me. Pro tip fellas: you’d get laid so much more often if you could manage to think ahead.
2 p.m. The gym is packed. None of my gym crushes are here and my playlist has gotten old. I’m in a workout slump.
4:30 p.m. Order groceries and plan to meal-prep for the week. (I say this every week and it usually doesn’t happen.) Chicken and veggie bowls for lunch and tacos for dinner. I’m on a mission to eat more vegetables, but it can be hard to do when you’re reheating lunch in a microwave.
11 p.m. Reading Empire of Pain, trying not to fall asleep. I’m so busy these days that I treasure the nights I spend alone. This phase of sexual exploration won’t last forever, so I’m trying to enjoy it without wondering what’s next.
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