In this week’s story, a graphic designer tries to rebound from a years-long situationship by having as much rough sex as possible: 38, single, New York.
DAY ONE
4 a.m. I’m wide awake and can’t fall back asleep; my throat feels tight and my heart is beating rapidly. I usually wake up early in the summer to run before it gets too hot, but I’d planned on sleeping for another hour. I take deep breaths, trying to coax my body into relaxing, to no avail.
I am fresh out of a yearslong situationship with an artist, N, with whom I was exceedingly sexually compatible. It wasn’t just that we both liked rough sex, but that he furnished me with sex toys and could anticipate what I’d like.
We met on Tinder. It started out casual, which was manageable at first because I didn’t respect him: He struck me as an art-world clout-chaser, a man holding out for the hottest, most influential woman who would have him. He relished being a fuckboy and bragged about his conquests. But he’d mellowed out, and I began to see him every weekend. We’d do things that weren’t sex-related — go to dinner, movies, concerts, the beach, the ballet. He’d even met my friends.
Then he came over one evening with a confession: He’d hooked up with a girl who works at a bakery near his apartment and who had asked him out. All this time, we’d managed to avoid defining the relationship, only addressing it circumspectly when I asked him, periodically, if he was “seeing other people.” He’d always say no, but would add that he was “tired of the apps,” the exertion of dating. I never asked for clarity, afraid it would scare him away.
I didn’t know what to say. But the next day, when I still didn’t feel any better, I made my own confession: that I was hurt and that I was only interested in one person — him. He balked, and told me he wasn’t ready for a relationship.
5:45 a.m. A silver lining: the breakup jump-started my fall marathon training. While running up a hill, I remember that I won’t see N again, can’t even just fuck him. But the ache in my legs and lungs eventually takes over and my emotions no longer preoccupy me.
9:15 a.m. My work day keeps me on the rails. But after sleeping only four hours a night for several weeks, I’m beyond tired. Luckily I do not have to operate any heavy machinery; all I have to do is design books.
1 p.m. No appetite since the breakup, but I take a lunch break and gulp down my nth coffee of the day. I open the apps and swipe, frantically. Running isn’t cutting it anymore; I need to be fucked, need to prove to myself that I can enjoy sex again.
6 p.m. From my mouth to god’s ear: A younger man, Z, staying in midtown, asks me to come to his hotel for a drink later that evening. I appreciate his boldness. And, if the shirtless photograph of him scaling a boulder is any indication, he’s attractive and muscular.
9:55 p.m. I’m back, I think to myself, walking to Z’s hotel. When I get there, Z, to my relief, resembles his photos. He asks about my job and what I think of the general layout of Infinite Jest, a challenging title to design due to the variety of paratextual elements, and the book’s length. I’m impressed by this question; Z was, in fact, listening to me explain what I do. We close out at the bar and hop on the elevator.
11 p.m. When the door slams behind us, Z takes off my dress and flips me around so that my head is hanging over the edge of the bed and starts fucking my face, one hand on my throat, and the other fingering me. I feel tears welling up in my eyes, partly because there’s a dick in my throat and partly because I feel close to coming: I was beginning to worry, irrationally, that it would never happen again.
12 a.m. As I walk toward the uptown 6 station, I feel something close to happiness.
DAY TWO
5:30 a.m. Since the dissolution of my situationship, every morning I’ve been obsessively checking my horoscope and performing tarot readings — doing “girl magic” as my friend’s husband calls it, derisively. I am desperate for something to jolt me out of my grief.
6:45 a.m. The running path in Central Park is packed with running groups, a now trendy activity for singles. But the fact that I’m annoyed seems to indicate that I’m less preoccupied with the breakup.
10:30 a.m. A slew of titles hits my department this week and everyone is feeling the strain. I feel compelled to take on my share of the burden, though I worry about getting everything done on time.
1 p.m. Lunch. I suck down another coffee as I check my messages and swipe compulsively. I get a prospect for the evening: D, a tech bro based in midtown. Like Z, he closes quickly: When I tell him that I’m looking for casual sex, he asks if I’m free for a drink.
7.30 p.m. D is at least a foot taller than me, broad-shouldered, and fighting back a dad bod — to be expected as we’re both near 40. He’s a native New Yorker and has a twin brother, “also on the apps, maybe you’ve seen him.” I haven’t, but this aside seems like a challenge. I tell him I’d keep an eye out.
9 p.m. D’s apartment reminds me of every man’s midtown studio: sparsely decorated, a print on the wall that looks like hotel art, a sofa of indeterminate style and color, a sparsely populated bookshelf, a robust work-from-home desk area with a very functional-looking chair, and a bed pushed up matter-of-factly against the wall with a window. But it is tidy.
On the sofa, D pulls me into his lap and kisses me. Despite our text exchanges about the various things I enjoy, he proceeds in vanilla fashion. But I don’t mind because he’s a man who knows what he’s doing: I come very quickly when he goes down on me.
DAY THREE
8:30 a.m. Frenzied swiping, again, on my commute to the office. Though I have plans to meet with my writing group in the evening, I’m keen on finding someone to fuck later.
12:30 p.m. Slammed at work today.
3 p.m. My projects are delayed because of one design that has been returned to me, repeatedly, for revisions. My jaw aches from clenching it all day.
6:50 p.m. I receive a message from a younger man, A, in town for a wedding. He asks me to join him for a drink at his hotel after my meeting.
7 p.m. Writing group. I have not been able to write since the breakup. Still, seeing my friends, offering feedback and support, makes me feel happy, part of a community.
10:30 p.m. I meet A at a bar in Fidi. He’s handsome and tall, from L.A. He seems too kind and well-adjusted to be seeking hookups; I wonder if he’s also newly on the rebound.
11:45 p.m. This man is a romantic in bed. He likes to kiss while we’re fucking, goes down on me for a long time, makes sure I come. He wants to hold me when we’re done. I’m reminded that I enjoy this affectionate style of sex. A sense of warmth and slowness creates a different kind of intensity, one that approximates emotional intimacy.
12:45 p.m. A says he’s frequently in town for work and would like to see me again during his next trip. I’m pleased. He calls me a car and asks me to text him when I get home. Big boyfriend energy.
DAY FOUR
8:30 a.m. I arrive at the sexual-health clinic early so I can return home in time for work. After years of having one consistent partner, I’m now back to my old routine of getting tested every couple of weeks.
1 p.m. Half day at work. It’s beautiful out, so I spend the rest of it at Orchard Beach.
6 p.m. My single prospect for the evening fell through: A man asks me to host, but I turn him down, too lazy to clean my apartment and change the sheets.
9 p.m. I can’t focus on the book I’m reading, so I spend the evening shopping online, buying nothing.
DAY FIVE
4 a.m. Awake before the alarm again. An evening without sex and my equanimity is already fraying at the edges.
11 a.m. I match with an artist, C, with whom I spend the rest of the day texting. I like his taste. He’s been reading Nathanael West, literary theory, philosophy. We plan to meet on Monday evening.
12:30 p.m. Meet my friend E at a book fair downtown.
5 p.m. E and I grab drinks and an early dinner. She’s into tarot so we talk about cards that have been haunting us. The moon card, which evokes dreams and intuition, has come up a lot for E, who is in a moment of transition as she wraps up graduate school. I tell her I’ve noticed the three of swords (disillusionment, heartbreak) as well as the devil card (addiction, lust) frequently appearing in my readings.
9 p.m. I go to sleep feeling grateful for the romance in my friendships, the way I’m able to give and receive the closeness and vulnerability I so desire among my friends. I wonder if this is enough.
DAY SIX
5:30 a.m. Can’t fall back asleep. I open up the apps and match immediately with a shirtless torso. S, the torso, is German and ten years younger than me. He asks if I want to come over to his place in Hell’s Kitchen; he’ll pay for a car both ways. I am feeling particularly horny and lonesome; Sunday mornings remind me of my ex. I could use the distraction.
6 a.m. The car speeds down FDR Drive — no traffic at this hour. I drop a pin at his address and text it to my friend W, my de facto emergency contact.
6:30 a.m. S, for all his talk about fucking me roughly and taking charge, rather lazily pulls me on top of him. So I ride him until I finish, which doesn’t take very long. After this, I feel tired. But S wants to keep going, get rougher.
At one point S is on top of me, and the pendants he’s wearing — a cross and a madonna icon — keep striking my forehead with each thrust. He’s Catholic, but when I ask him about it, he clearly wants me to stop talking.
8 a.m. The sex is starting to feel tiresome. His heavy breathing irritates me, and my thighs feel chafed. He wants me to stay until noon. No way. I get dressed and he doesn’t stop me.
2 p.m. Laundry. I unload sheets N has slept on into the wash, and resist the urge to smell them.
7 p.m. Late exercise class and then early to bed.
DAY SEVEN
8 a.m. I pick up my box of “Oblique Strategies,” a series of cards with aphorisms that the electronic musician Brian Eno made in 1975 — basically self-help for artists. They always help me when I’m stuck. I pull one that has a famous prompt: “Honour thy error as a hidden intention.”
11 a.m. Already swamped at work!
4 p.m. I feel less agitated about my incredibly busy day because I have something to look forward to: meeting up with the artist in the evening. I’ll head home soon to start getting ready.
9:30 p.m. I’m fucked, I think, when I meet the artist, C. He’s attractive: tall and thin, with short gray hair, blue-gray eyes. He arrived dressed in a white linen shirt and trousers, very elegant. Our conversation is easy, having already crossed a certain threshold of intimacy after sexting the last few days.
10:45 p.m. C’s apartment is tastefully appointed and minimalist: It’s tidy, spacious, with custom-built shelving and a seating area. It’s the way I’d decorate my apartment if I had a bigger budget. Concerning because I tend to fall for men who embody or have something I want for myself, like a disciplined creative practice, good taste, hotness, success in their respective field, etc. That by “possessing” them, I can acquire these desirable things for myself by association.
11:30 p.m. I come hard when C fucks my ass and strokes my clit, speaking to me urgently in French, his native language. No idea what he says but it sends me over the edge. Good sex will always blind me from seeing what isn’t working.
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More From This Series
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- The Musician Who Ghosts Three Dates in One Week
