sex diaries

The Paralegal Who’d Rather Not Commute to a Date

Photo-Illustration: James Gallagher

This week, a future law student looking for a date close to home: 22, paralegal, straight, Bushwick.

DAY ONE

6 a.m. I wake up, study for the LSAT, then go for a run. In my ideal world, this is what every day is like. In reality, this happens once every two months.

9:30 a.m. I’m at work on time! I’m a paralegal in a prosecutor’s office and I really like it. I’m planning on working in politics/government/public service of some kind. Law school, Big Law and/or Feds, public office. Ideally, that’s how it all goes down.

7:30 p.m. I take the L to Williamsburg for a first date with a guy I met on an app. I’m constantly busy, with work, studying, socializing. This is primarily because I grew up in NYC and I’m back here after college (plus, 80 percent of my college friends moved here, too).

9:10 p.m. The date, T, finally arrives. We stand at the bar for a while before I snag a table. He’s cute but not on my level intellectually and I feel like I need to slow down for him. I’m thinking it’s a meh date. This is my barometer: If I feel like I need to slow down the speed and sophistication that my brain operates at, he’s not serious dating material — and that’s why I am rarely seriously interested in guys. I’ve never been in a long-term relationship before, and I haven’t really felt the desire to.

I also don’t feel the itch to get into a long-term relationship because I’ve known for a long time that I don’t want kids. And I’m planning on being in law school either next year or the year after, not in NYC. I’m in a transient space career-wise and life-wise. Not the time for monogamy.

11:09 p.m. R, someone I’ve slept with a few times, texts to ask how my weekend was. I told him I went to the Mitski concert, and joked that I needed eight more piercings and three more tattoos to fit in. He says my curves drive him “INSANE.” He earns the nudes I Snapchat him for the next hour as I masturbate. We make plans to meet up later this week.

I like R. He’s the one person I’m dating that falls into my three categories for sexual partners: smart/ambitious, hot, and age-appropriate (27). He’s a little more bro-y than other guys I’ve been into, but I like it. We’ve only actually slept together twice, but the sex is probably the best I’ve ever had and I just feel comfortable with him. I think we both feel similarly about each other — happily surprised that we got along so well in bed and as people from the start, and just wanting to continue that. He’s a corporate lawyer and an Ivy League snob like myself. He talks constantly and never asks me about myself, and I don’t really care.

DAY TWO

9 a.m. T sent me a few texts. I’m just not sure about pursuing this one.

12:21 p.m. A texts me to confirm our date tonight. We connected on an app and made plans a couple of days ago. He seems a little weird but I trust him because his texts are long and articulate. Part of the reason I’m messaging him is because he’s experienced in BDSM. I’ve been somewhat bored by some of the sex I’ve been having recently and am into the idea of experimenting with someone respectful. A also lives like two blocks away from me, and I could use a hookup that doesn’t require a commute.

7:40 p.m. I meet A at a bar about a block from our respective apartments. We chat for a while. He’s really intelligent. He’s a poet/photographer/graphic designer and the kind of person I hoped I’d meet in Bushwick. He identifies as agender and is cool with they/them or he/him pronouns.

9:30 p.m. After two drinks, we go back to his place. I blow him for a while, which is difficult because he truly has the largest dick I’ve encountered and I don’t have that much experience with BJ’s — I had sex for years before I chose to give one. Then we fuck, pretty straightforwardly, but I really enjoy it. He has SEX KITS around his room. He keeps the vanilla one next to his bed — lube, condoms, multiple vibrators, one of which he gives to me to finish. We watch TV, then I leave. I’m not super attracted to him, but really do want a Bushwick fuckbuddy.

DAY THREE

9:30 a.m. I want one of the lawyers I work with to ask me what I did last night so I can smile mischievously. They’re all so hot. Ugh. And married.

4:41 p.m. I get a “What are you doing tonight,” from T, who I went on that meh date with. I’m still surprised when people want me after meeting me.

My self-esteem and sex life were not great in college: I had a pretty bad eating disorder for a lot of it and turns out when you’re underweight one of the (many!) side effects is a lack of sex drive. Only now, chubby and horny again, do I realize how much I was missing.

But the latter two years were defined by me gaining a lot of weight back and then not feeling (I think validly) sexually-valued among my male peers. I was a great, randomized controlled study because I was skinny the first couple years, and then progressively not over the next couple, and the way people treated me changed drastically. Professors, peers, men, women … I have so much anger about this — not as much for me personally, but for what it says about these places that think they’re so woke.

5 p.m. R asks me what I’m doing tonight. We plan to be in touch later.

5:25 p.m. I get a “Maybe we should just be friends” text from last night’s B. I try not to let it bruise my ego too much.

9:51 p.m. R suggests I come to the party he’s at. This is cool. Again, I still expect to be hidden by guys.

11:03 p.m. I leave to meet him. I bought this long shimmery black dress today and I’m wearing it sans bra.

11:30 p.m. I get to the party and am greeted by this warm, WASP-y, beautiful blonde woman who has no idea who I am, but when I tell her I’m here to meet R she whisks me in, hands me the “signature cocktail” of the party, and takes my coat. R sees me across the room; we move toward each other. He’s grabbing my wrist and pulling me across the room.

I’m still deeply insecure about being desirable as a public partner for people and so I LOVE him introducing me to his friends, I LOVE hearing people say, “Oh yeah R said a girl was meeting him here, it’s nice to meet you.” I love positioning myself next to him. And I love when R leans over and whispers, “Let’s get out of here.”

1 a.m. R doesn’t like blow jobs, which I am happy with. We get to it pretty quickly. Mostly missionary and its variations. He likes putting my legs above my head for an intense version of it. The last time we hooked up before this was the hottest sex of my life — 8:30 a.m., doggy, with him pulling my hair to arch my back. But sex with him is always good.

When we’re done, we clean up, talk for a little, and go to sleep. Or rather, he does. I can’t sleep with other people.

DAY FOUR

10 a.m. We wake up, just talk, drink water, no sex. I go back to Bushwick.

6:20 p.m. I get to a middle-school reunion. Everyone is mostly still lame, but I’ve known these people since I was 3 so there’s an easy intimacy. Some of us get dinner after. At one point I describe my sex life as “chaotic” to the table.

11 p.m. I get to a birthday party with a bunch of very older cool alumni from my college that I think are rad and am trying to see more of. I get super drunk on red wine and go back to my parents’ place uptown (where they live, where I grew up) to sleep deeply.

DAY FIVE

2 p.m. I want to do something tonight, so I hit up a few different guys. T responds first. Lucky guy; I guess I’ll give him another try. We make plans to meet near his place (my suggestion) after I go to a family gathering.

7:25 p.m. I get to the bar in Bed-Stuy to meet T. After he finishes his second beer he says, “Maybe one more than we can head out?” which I take as a good sign. We seem to be clicking more on this date.

8:50 p.m. He says we can go back to his place if he’s interested. I tell him yes.

9:30 p.m. The sex is good. He lights some candles, turns off the overhead lights. He fingers me while I blow him for a while. I’m always really confused when I see an uncircumcised dick and then I remember oohhhh right that’s what that looks like. We proceed to have some really, really, good sex.

Before I leave, I ask T about his sex life and he says he’s actually in an open relationship with someone who’s in London now. This is great news for me, because I don’t LIKE-like him and don’t want to be in relationship, but this sex was good and he lives not too far from me.

10:45 p.m.  I come home, masturbate while alternating between porn and Vox.com. Bliss.

DAY SIX

10:09 a.m. I message T that I had a good time and I hope he did too. He says yes and re-emphasizes that it has to be casual and asks about STI’s. Very responsible.

11:38 a.m. D, an old friend who I lost my virginity to, and I have plans tonight. I rearrange my night so that we have time to fuck before I see my friends for dinner.

6 p.m. I get to D’s house. We small talk and drink a few sips of wine before he lowers the lights and we get to it. We switch between doggy and missionary. I shower off and then go meet my friends for dinner.

8:10 p.m. I eat dinner with my friends on the Lower East Side. I love my friends so much; it’s just a really lovely night. That is all.

10:30 p.m. My pants literally have white stains on the crotch. UGH.

DAY SEVEN

8:46 a.m. I have a few texts from T. He mentions anal. I say we can make very tiny steps in that direction.

12:28 p.m. Another guy I’ve been messaging with on an app, P, and I decide to make plans. I tell him to meet me later at a cool-kid pizza place with natural wine.

8:10 p.m. P gets there while I’m in the middle of tasting different wines. I don’t LOVE his personality, and he comes off as not a super-critical deep-thinker type. But whatever.

9:10 p.m. He says we can go to a different bar, or that his house is right nearby and he has beer and wine. I’m down.

9:30 p.m. He opens a bottle of wine and somehow we start talking about sex. What we like, our past relationships/experiences, etc. After a while I ask if we can just get to it. Honestly, I’m pretty annoyed by his personality and don’t want to dislike him even more before using him for sex.

10 p.m. He eventually puts on a condom and we fuck. Missionary for a while, with my legs eventually getting above my head. Then we switch to doggy. He doesn’t have lube, which … if you don’t have lube, you’re not a feminist.

11 p.m. Heading home. This has been a long week, and I think I need to take a break from men. Maybe I’ll go celibate in January …

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The Paralegal Who’d Rather Not Commute to a Date