sex diaries

The Product Manager Who Would Sleep With Every Person in New York City

Photo: James Gallagher

This week, a product manager distracting himself from his broken heart with sexting, drugs, and creative writing classes: 29, straight, single, Bushwick, product manager at a startup.

DAY ONE

6:30 a.m. I wake up and force myself to go for a short and unpleasant run. I’m in much worse shape than I was when I lived on the West Coast — too much drinking, drugging, and partying on weeknights in New York.

7 a.m. Thinking about my ex, as usual. We were together for a year and a half; she broke up with me two months after I moved to New York to be with her, saying I was “emotionally unavailable”. After we broke up I went on an absolute tear — I slept with seven women in eight weeks, mostly one-night stands, and just generally tried to distract from my grief as much as possible. It probably wasn’t the healthiest response, but I’d rather be miserable and slutty than miserable and celibate.

1 p.m. I text L., my recent hookup buddy, to see if she wants to hang out tonight. I was sure L. was a bot when I matched with her on Tinder — her only photo was her topless with emojis covering her nipples. But she was real, and we’ve been fucking like crazy the past few weeks.

2 p.m. I recently got in a little trouble at work for slacking off too much (I’m a product manager at a tech startup), so I’ve been working extra hard lately. And it actually feels good!

2:30 p.m. L. tells me she wants to see me tonight and I respond by telling her I’ve been obsessively watching the sex tape we made a few weeks ago. Then I wonder if “sex tape” is an outdated term, since we’re all filming on our phones now. It probably is, but I can’t think of anything better.

8 p.m. Sitting in the fiction-writing class I started taking on a whim after my breakup. When I first signed up I thought I’d be scoping it out for cute women, but there’s only one cute woman in the class, and her writing is so bad that I could never be interested in her.

11 p.m. Over at L.’s place. She usually wants really rough sex — choking, slapping, bossing her around, etc. — but we’ve both had long days and neither of us are really feeling it, so we have a fairly vanilla quickie instead.

11:30 p.m. Ever since my ex told me I was too emotionally closed off I’ve been making a conscious effort to be as open as possible with everyone in my life, so when L. asks me how my day was, I actually tell her instead of just saying it was fine. That may not sound like much, but it’s a big deal for me.

DAY TWO

7 a.m. I have a story due in class next week that I haven’t been able to get to, so I wake up early and take an Adderall to pound some of it out. I have a love/hate relationship with Adderall and try not to take too much of it. It helps even more with writing fiction than it does with less-creative work.

11 a.m. Adderall always makes me insatiably horny, so I’m sexting from work with H., who’s been my on-again, off-again sexting buddy (and occasional real-life hookup partner) for five years. We met on OkCupid, back when that was still cool. Hard to believe I’ve had a sexting buddy for half a decade — in some ways it’s the longest relationship I’ve ever had.

My relationship with sexting can get pretty addictive at times — my natural impulse is to distract myself from unpleasant sensations whenever possible, whether through sex, drugs, or whatever else is available. I’ve gotten a lot better at being present since I started meditating five years ago, but there’s still a long way to go.

10 p.m. Smoking a joint in bed and browsing couples on Feeld. I’ve had a few threesomes and foursomes in the past and am trying to explore that side of myself more. So far I’ve made plans with two couples and they’ve both ghosted me at the last minute. I suspect it’s pretty common for couples to think they want to invite someone else in and then realize at the last minute that they’d rather keep that a fantasy.

DAY THREE

6:30 a.m. Up before my alarm goes off, again.

6:45 a.m. I force myself to go to the gym. I’m naturally very skinny, which has its upsides (eating whatever I want) and downsides (having to work out a ton to look even moderately fit).

9 a.m. On the L train, I think about how lucky I am that the slightly nerdy look is considered hot in 2019. If this was 1980, I would be way less successful with women.

1 p.m. During lunch with a college ex, she tells me that I’m not a good person to casually date: “You’re complicated and moody, so if there isn’t a big reward at the end it’s not worth it.” She still knows me so well.

4 p.m. I get a text from A., someone I’ve recently started seeing, who I met at a summer arts camp years back. She has what she thinks is a UTI, so she’s out of commission. I’m weirdly nervous to ask if she still wants to hang out — being rejected as a friend would hurt way more than being rejected as a sex partner. Besides, A. is intimidatingly cool. She dropped out of high school to become a stand-up comedian, and she’s tall, androgynous, and covered in tattoos.

4:30 p.m. A. says she’s happy I still want to hang out and also that she’s at the doctor’s office and that her UTI might actually be chlamydia. We’ve always used a condom, so I’m not too concerned, but given how promiscuous I’ve been lately this would not be a good time to have to get in touch with all of my recent partners.

8 p.m. At home and packing up my stuff — I’m moving in with a friend in a few weeks. Living alone was great when my girlfriend was over all the time, but now that I’m single it’s not worth the price premium. Admittedly, living alone is better for dating, but it’s not $800/month better.

DAY FOUR

11 a.m. My regular weekly phone call with my parents. My relationship with them has gotten a lot better since I’ve internalized the fact that I’m a grown man and that constantly rebelling against them stopped being cool a decade ago. Plus, they’re happy that I’ve moved closer to home.

3 p.m. Bored and browsing Tinder. My approach to Tinder is incredibly lazy: I pay for the upgrade where you can see who likes you, and then just pick from those people.

I generally enjoy dating — there’s something fun about meeting new people, even if they suck — but after my initial post-breakup binge wore off I haven’t been able to get back into it. Everyone pales in comparison to my ex. Besides, now that I have a couple regular sex partners the effort/reward ratio of dating just isn’t worth it a lot of the time.

My ex and I have exchanged a few emails since breaking up, but beyond that we haven’t been in touch. It’s still too raw. I’ve exhibited an unusual amount of self-control in not stalking her online at all.

11 p.m. On my way to a party at a co-worker’s place. I’ve lived here for six months and I still can’t get over how hot everyone in New York is. I would fuck every single person in this city.

1 a.m. Doing coke in someone’s bedroom with some co-workers who immediately pegged me as a fellow drug person. I’ve never been all that into coke, but it’s everywhere in New York.

2 a.m. Home from the party when L. invites me over. I reluctantly tell her I’ve done too much coke to fuck tonight. I think I’ve found a good reason to do fewer drugs.

DAY FIVE

10 a.m. Morning meditation. This used to be a daily thing for me, but I’ve been slipping lately, and I’m trying to rededicate myself to my practice this month.

11 a.m. Sexting with H. again. Our sexts always follow the same pattern: a few quick texts and photos, maybe a video or two, and then we watch each other finish on FaceTime.

11:30 a.m. A. and I are still trying and failing to find a time to meet up. I find myself thinking about the last time we fucked — right when I was close, she looked me in the eyes and told me to come for her, which I thought was pretty brazen given it was only the second time we’d slept together. Lately I’ve been really into looking into people’s eyes during sex, even if it’s just a random hookup. Clearly I’m craving intimacy.

2 p.m. Over at L.’s for another quickie before she leaves on a weeklong trip to Spain. She loves being dominated, so lately I’ve been doing this thing where I push her to her knees and make her start giving me head the second I walk into the door. Most of the time I can get into the dom stuff, but there’s always a little part of me that feels like I’m in an improv troupe, playing a cheesy character.

10 p.m. Slow rest of the day. I work on my piece for fiction class and fall asleep smoking weed and watching Adventure Time.

DAY SIX

11 a.m. Reading about the new abortion restrictions in Mississippi and Alabama. I got someone pregnant a few years ago and took her to get an abortion, and I’ve been debating saying something about it publicly for a while now. I think it should be on men too to speak out about their abortion experiences. But I’m not sure how to do it without seeming somehow performative.

2 p.m. Almost no meetings at work today, which is unusual. I alternate between getting things done and thinking about my ex.

4 p.m. Bored and Tindering. I’d like to be in another relationship eventually, but I know I’m not ready yet, so in the meantime I’m being pretty open about just wanting something casual — my Tinder bio is “Running as fast as I can on the hedonic treadmill.”

8 p.m. “Girls’ night” with my friend E., which basically means booze, coke, and gossip. E. is a friend from college and also the wife of one of my closest friends — I’m the one who introduced them, which sometimes feels like my most meaningful accomplishment on this Earth so far. We mostly talk about my ex and how badly I’m still in love with her.

12:30 a.m. In bed and Tindering again. Why am I even doing this?

DAY SEVEN

8:30 a.m. I wake up hungover and dash to the office, with a quick stop for a bagel and cream cheese on the way. Drinking on weeknights does not agree with me, and the coke probably didn’t help either.

10 a.m. Text from A. Turns out she doesn’t have chlamydia, just some weird non-STI infection. Great start to the day. I’ve already had chlamydia once and did not want to go through that again.

8 p.m. With my friend B. at this comedy show where two strangers go on a blind date in front of an audience. It’s unwatchably bad, one of the worst shows I’ve ever seen. But even a show this terrible is enough to make me miss my ex. I think that once you’ve been really in love with someone, some part of you stays in love with them forever.

11 p.m. I fall asleep sober for the first time in four days, still thinking about my ex …

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The Product Manager Who Would Sleep With Every Person in NYC