sex diaries

The Designer Telling Her Ex She Wants to Sleep in His Bed

Photo-Illustration: James Gallagher

This week, a woman hooks up with an old flame after a confusing breakup: 35, single, Brooklyn.


9 a.m. Settle in for a long day of work: I’m a graphic designer, so I’ve been working at home for a while now. I have a weekend trip to my college town planned, which I’m really looking forward to as a way to distract myself: A few weeks back, my boyfriend of ten months abruptly broke up with me over text.

3 p.m. I try to focus on work, but my mind yanks me back to the moment my (now ex) boyfriend, B, and I last spoke. Our argument was inane: I made a dumb joke about working for a defense contractor so I could pay off my student loans, which he took way too seriously. What ensued was a long argument about privilege — he’s a straight white guy with two Ivy League degrees — that ended with him storming out of his apartment.

The next night he texted: “Hey M I want to break up. I’m really sad but yesterday was too much for me.” He said my things were ready for me to pick them up. I couldn’t believe the proverbial Post-it breakup — the terse, chillingly casual, and one-sided termination of a relationship — had happened to me.

And now, weeks later, I’m still thinking about it all the time. Exhausted, I take a nap.

7 p.m. Wake up from the nap. Normally, in the aftermath of a breakup, I’m addicted to Tinder: Matching gives me a dopamine kick and hookups temporarily abate my anxiety. This time, however, matching did nothing for me. Even more concerning, I wasn’t feeling horny at all, just tired. I didn’t particularly enjoy sex with B: He fucked me impassively, just pile-driving it in there, eyes closed.

I remove “enjoys sex” from my bio to see what will happen. Predictably, my number of matches went down. But I feel apathetic: I don’t want to meet anyone who likes me without the apparent guarantee of sex — it seems like too much effort to get in bed with them, or leave the house.


4:30 a.m. I wake up early and can’t go back to sleep, so I pick up my book.

8:30 a.m. Start work in a frustratingly slow fashion. I cancel lunch plans with a friend because I’m already behind on my day’s tasks.

5:30 p.m. I meet my friends H and J at at museum. It’s too early to take advantage of free admission, so we grab a drink at a bar. We discuss J’s fear of catching feelings for a new flame, a fear to which I can relate — falling head over heels and getting hurt is a calculated risk in dating. H, a man of consummate detachment, advises only half-jokingly: Don’t worry, there’s always more dick. I envy H’s clean division between sex and emotion. After fucking someone a few times I almost always want them to commit to me.

11 p.m. Tomorrow I’m leaving New York to visit my old college town. L, a man I dated seven years ago, texts to ask if I still plan to crash at his place. And, he adds, I can sleep in his guest bedroom or in his bed. I thank him for the option and tell him I’d like to sleep in his bed.

This decision, he says, makes him hard. He asks how badly I want to be fucked. I’m taken aback — he’d been so coy about letting me “sleep in his bed.” When I take too long to respond, he apologizes effusively for steering the conversation to sexting. Worried he’ll have second thoughts and ask me to sleep in the guest bedroom, I send a hasty, uninspired response: “Good! I can’t wait!”


9:30 a.m. At Grand Central, I hop on the train out of town. I have plans to meet with old friends: G, who had a baby during the height of the pandemic; and S and E, who recently moved into a new house together.

12:30 p.m. On the train, I listen to wistful music. I feel apprehensive as the train pulls into the station: I begin to recall the failed relationships, stunted career prospects, and general unease I associate with my life here.

1:30 p.m. G and I meet up for a walk in her neighborhood. Pushing the stroller conveying her napping child, G updates me on her life: She’s bought a house in the next town, published two children’s books, and is parenting a toddler. I’m impressed by her growth.

I tell G that I will be crashing with L. She is surprised I still talk to him after the abrupt end of our relationship: Upon L’s return from a friend’s wedding, he informed me, while we were in bed, that he’d met someone at the wedding and that they were in love. She was flying out to meet his parents the following week, he said. I was stunned and humiliated. Three years later, I heard from L again: He told me he was now divorced from her, and apologized for the way he treated me. I felt vindicated; now my misery was counterbalanced by his.

G mentions that her husband ran into L in town one day, and he said he regretted breaking up with me. I’m flattered by this story. I wonder if he thinks about me a lot, and I hope he does.

5:30 p.m. S, E, and I make a toast to new beginnings over dinner. After dinner we migrate to their new place, a beautiful Victorian with stained glass windows and an actual solarium. With drinks on the porch, we talk about cryptic text messages, about our fears of getting hurt again, about failure. It is therapeutic to speak so freely about what scares us.

10:00 p.m. I text L and tell him I’m heading over. He is out walking his dog and suggests we meet halfway and finish the walk together. L gives me a tour of the changes made to the city since I’d left: We walk past several newly constructed residential colleges, designed to emulate, uncannily, the neo-Gothic style of the old campus buildings. There are new cafés, condos, and expensively landscaped areas that bear no resemblance to the places I remember.

10:30 p.m. We approach a row of townhouses and walk up the stairs. He finally received tenure, which encouraged him to buy this stately home. Inside, he gives me a tour of the house: It has a nice study, three bathrooms, and built-in bookshelves in every room of the house. This is more space than a bachelor needs, but I suspect that he does not intend to live here alone.

We sit on the couch and get high while catching up. I tell him about my job (still low-paying, but no longer soul-killing), and where I am living now. He discusses his never-ending book project, some new developments in his department, and makes vague reference to a bicoastal relationship that seemed promising but didn’t work out for obvious reasons.

11:30 p.m. It is getting late and L still hasn’t suggested that we go to bed. So I tell him I am tired. I feel silly for making an oblique reference to sex; why can’t I just say it out loud. No matter because he understands what I mean.

L is not adventurous nor particularly expressive, but he has one job and he does it well: He regards my body appreciatively and attends to it knowledgeably with his hands and his mouth, letting me come first. He fucks me with affectionate gratitude, which makes me feel powerful but also makes me wonder if he hadn’t had sex in a while.


10:30 a.m. We wake up late. L’s dog is desperate to go outside so we get dressed and go for a walk. Upon our return, he makes omelets and we read the newspaper. It is the vision of the intimacy and lived-in-ness I want from my relationships, but I suppress my delight. I can’t let myself get too comfortable, especially given my fraught history with this man.

I tell him he can get started with his day. However, because my departure time is approaching, it seems pointless for him to absorb himself in work only to leave about an hour later. There is only time for one activity. To my surprise, he unceremoniously asks if I want to have sex again before I go. I do.

12:15 p.m. L drops me off at the train station and his anxious dog, who gets triggered when people leave, barks at me. He has a place in New York, so my parting words are: I’ll see you in the city. I immediately regret making the implication that I want — and expect — to see him soon.

5 p.m. I’m back at my friend’s place. I reflect on my weekend with contentment and a sense of triumph: I’d had meaningful conversations with old friends and managed to make my ex want me again — a cosmic victory. It is enough to anesthetize the sting of my most recent breakup. I sleep well.


9 a.m. I’m still coasting on the euphoria of my weekend. I try to sublimate this energy into productivity at work.

11 a.m. I think about sex with L and how much I enjoyed it. I think appreciatively about his newfound stability and prestige: tenure and a townhouse. Given my relative precarity in life, the prospect of hitching myself onto his wagon is very tempting.

5 p.m. I spend all day thinking about L and imagining a future with him. I text my friends for some perspective and to be reminded that this man has not given me any indication that things will be different this time. In all likelihood, he will bail on me again.

11 p.m. I can’t sleep.


11 a.m. I consider reconnecting with a dom I haven’t seen since I’d started dating B. But I am too busy at work to pay him a visit and I can’t summon the will to leave the apartment.

4 p.m. I text L to inform him that a concert he’d wanted to attend has been rescheduled due to the incoming storm.

6:30 p.m. L texts back: He can probably attend the rescheduled concert because he doesn’t have to teach that day. I “tap back” a heart symbol in iMessage.

11 p.m. I fight the urge to text more.


7 a.m. It is an overcast morning. I enjoy the gloomy weather with coffee and my book. The attachment for L I’ve been resisting feels slightly less acute. If nothing else, seeing him brought back the post-breakup horniness I thought I’d lost.

2 p.m. I re-download Tinder and create a new profile. I reinstate “enjoys sex” into my bio.

7 p.m. Outside, it rains unrelentingly. I’m grateful to be inside, dry, and on the second floor. It is a big night on Tinder—– most people heeded the flash-flood warnings and remained indoors with nothing to do but swipe. The influx of matches buoys me. I feel desirable and fuckable.

I admit that my notion of stability is idealized, and that I don’t actually know what it means to have stability in a relationship. What I do know: It isn’t an elaborate breakfast cooked the morning after hooking up with your ex.

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The Designer Telling Her Ex She Wants to Sleep in His Bed