The 36-Year-Old Writer Sending His Ex a Very Long Letter

In this week’s story, a writer of horror fiction starts falling in love, then gets dumped in an Uber: 36, single, New York. 

DAY ONE

8:52 a.m. I roll out of bed eight minutes before I need to sign on for work. I have a temporary (and well-paid) gig as a writer for a large nonprofit, but I think of myself primarily as a horror writer. (I have a newsletter in that genre.) I hate the hustle, but I love to write.

1:11 p.m. During my lunch break, I take the train from my apartment in East Harlem down to Prospect Park and text L that I’m here. We met at a middle school in Tribeca last year, where I taught seventh-graders creative writing once a week, and she planned events. I felt drawn to her from the moment we met, but it wasn’t until I saw her on a dating app a month ago that we started hanging out, and the vibe since, four dates in, has been electric.

I’m technically working, but I’m remote today so I can pull this off. L brakes her bike to a stop in front of me; she has incredibly long hair and isn’t wearing a bra. My type. We make out on the grass for an hour, snack on dates dipped in tahini, then bike back to her place in Sunset Park.

We walk up the steps of her brownstone and talk about zines; she’s been a collector, creator, and all-around zine stan since she was a teenager. Her apartment is sunny and spare. Like me, her bed is a mattress on the floor, and also like me, her room is covered in images of her creations and inspirations.

She drops to her knees, looks up at me with her big eyes, and lowers my shorts. She takes my hand and puts it on the back of her head until we find the rhythm. When she pulls back for a breath, we switch and I go down on her, and I can feel her entire body shiver when she comes. She comes like that one more time, then again after we have sex. Afterward, we lounge on her mattress. I admire her art.

5:10 p.m. Back in my apartment uptown, I check my email and Teams and respond to a few alerts, nothing urgent.

6:30 p.m. Caught up, I spread open a few notebooks and jot down notes from my time with L.

8:08 p.m. L texts a celebratory Mac Miller song. I heart it and respond with my latest love, a perfect song by Billie Eilish.

DAY TWO

8:08 a.m. I’ve been up for a few hours, but I don’t text L. I like the slowness. It took me a while to reach out after our first date, which was warm and wonderful, the kind of comfortable afternoon that can really set you up for a lifetime with the person. When I did I said something like “Dang that was so much fun! Let’s do it again soon” but with no plan or next moves. When she responded, a day later, to ask “so when you gunna ask me out on a second date huh?” I melted.

10:32 a.m. It’s a workday in the office, which I don’t hate at all, a big building in midtown that’s literally five stops south on the 6. I tweak text on corporate emails, watch videos from recent events to find content worth mining, and print 30 copies of my latest zine (34 pages each!) during lunch, when no one’s using the printer.

I think about L throughout the morning. Realize I really like her. For some reason it’s a huge shock, but the feeling is also radiant, the four cupboards of my heart fluttering open.

My agent emails an update on the book pitch we spoke to an editor about earlier in the month. Positive news, but no contract yet, and I’m hesitant to get too excited, especially after last summer, when I had a long video call with an editor who raved about my novel only to have the marketing team ax it. That sent me into a prolonged depression I don’t know I’m fully out of. Something about L feels like a shift. Maybe I just want it to.

2:34 p.m. W texts, asking if I’m free tomorrow night. “We can drink spiked tea and fuck on the roof.” I’m not terribly into W. We met at a friend’s party earlier in the summer and the sex is fine and she’s cute enough, but L’s been my heart’s focus. The text is enticing, though.

2:40 p.m. Immediately after solidifying plans with W, I feel a thing in a part of my body and text L to ask if she’s free two nights from now. Absolutely, she responds, in what feels like record time.

9:04 p.m. I keep listening to the Mac song L sent, been bumping it on and off throughout the day. I think part of a crush is carrying into sleep with you the sounds and memories of the one you keep seeing, the one you keep wanting to see. You hope they’ll be there in the dream.

DAY THREE 

4:08 a.m. I wake up mad early because I love my corner of the city when it’s finally quiet out. I prop open a notebook and capture some stray thoughts.

I’m a Pisces artist writer boy. Which means I’m a 36-year-old 6-year-old whose eyes spill like the ocean over things that do not warrant such reactions. And I fucking love writing it all down.

5:30 a.m. I make a cup of coffee and start a story. Get down 700 words. I like how this one’s shaping up. It’s easy in the way good art is, a pure fruit plucked at perfect ripeness.

9:08 a.m. I text L good morning.

2:02 p.m. Work in an office sucks. Seriously, what the fuck is this?

2:46 p.m. I make the day’s sixth, and I hope final, cup of bad coffee.

6:36 p.m. I CitiBike through Central Park to W’s place on the Upper West Side. We have bad sex. W’s a blowjob queen, which just means she initiates frequent and enthusiastic make-out sessions with the whole area and only stops if and when I direct her to. This time it’s no different, one of those surreal sexual experiences where my dick is in her mouth two minutes after I walk into her apartment, largely at her pull. Only this time it’s weird, I’m not getting it up. This doesn’t usually happen.

We stop, chill, hang out. I go down on her, think of L, get really into it. We stop and lie on her bed, passing around a half-joint while half-watching The Good Place. There’s a feeling of finality in the air. I wonder if she feels it, too.

8:08 p.m. Back home, I text L about Mac Miller and feel the vibes strong enough to get hard.

I put on my writing jacket, which is what I call the jean jacket I wear when making my art, and sit at my writing desk.

DAY FOUR

9:23 a.m. Another remote workday. I spend a good chunk of the morning chopping up printed pages of my zine with the paper trimmer I bought online, then using a heavy-duty stapler to bind them together.

11:24 a.m. I CitiBike through northern Central Park, feeling dumb and light and other words associated with pre-pre-love.

3:36 p.m. Sex with L at her apartment. It’s as great and fun as ever. She spends a lot of time riding me while facing me, which enables kissing. God her face is so nice to open your eyes to after minutes of lips and tongues and teeth. She smacks my hands on her ass and titties every now and then.

During a break, we talk about art and freedom and sex and love, and she bristles at my use of the word “normie.” A conversation about artists versus non-artists follows. The moment feels off. It rattles something in me I try to ignore. We eat peaches in her kitchen, naked, but for the first time at our parting, there’s no kiss good-bye.

4 p.m. Ten minutes into the Uber ride from her apartment to my sister’s in Crown Heights, I get a text. It’s from L. “You free for a quick phone call?” I say sure and pick up on the first ring.

I listen in silence as she tells me that she sat in her body after I left and something felt off and that she’s enjoyed getting to know me this last month but she doesn’t think we should keep seeing each other. It’s hard to think amid the explosion.

4:15 p.m. I ride the car to my sister’s apartment in perfect brokenness. When I get there I’m too miserable to play with my niece and nephews.

9 p.m As I try to fall asleep back home, something tells me this misery isn’t going away anytime soon.

DAY FIVE

11:34 a.m. I’m miserable. Can’t do shit other than watch true crime.

12:04 p.m. I don’t touch any of my work. I wonder if I ever will, or if it’s now too tied up in sadness.

1:08 p.m. I think of what a friend said recently. Crushes are just a lack of information. She said it with a tinge of embarrassment, like it was a cliché, but it hit me with profundity.

2 p.m. I try to focus on ways I didn’t click with L. She used phrases like “loosey-goosey” and “nitty-gritty” and got mad when I said “girls” instead of “women,” even though I also said “boys” instead of “men.” She didn’t offer an original verse during the song game in the park. She freaked out when I tried casually taking a Polaroid of her the first time she came over. Okay, I said, and lowered the camera. That’s not chill, I said in my heart. But she was so fine, I didn’t mind. Most of all, I think of how she ended it. You wonder how some women can be so cruel.

4:56 p.m. Listen to a lot of Olivia Rodrigo. Both albums, but not The Hunger Games song. It helps. Hit the bong hard and frequent. Sadness arrives, hugs, overwhelms.

6:57 p.m. I text O, who I met at a July Fourth party. I went out with her roommate a few times, but on our third date, she explained her soon-to-launch business: a meal plan for people with eating disorders. That was it for me.

O, though. She has this elfin face, and a blissfully round ass. We make plans to meet up for a drink this weekend.

11:47 p.m. As I fall asleep, I start drafting a letter to L in my mind.

DAY SIX

7:05 a.m. I pull my notebook under my blankets and spill out miserable thoughts and feelings like I’m actually convinced externalizing them will keep them out. I don’t think writing is magic, but I also sometimes do.

12:05 p.m. My sister-in-law texts me three separate pictures of women with descriptions of each. A friend of hers is trying to set them up. This depresses me. The women are all attractive, accomplished, available, but my heart’s been stabbed so murderously that I just want to burrow in forever.

3:04 p.m. In between the writing I’m getting paid for, I draft a letter to L.

8:05 p.m. By the end of the day, I have 1,700 words. The plan is to reread it in the morning then send it over.

DAY SEVEN

8:08 a.m. I reread my letter to L, make a few minor edits.

8:40 a.m. I read it one more time, put it in a Google Doc, and text it to L.

8:46 a.m. Within minutes, she responds. She’s very touched and emotional (“uve got a girl crying on the subway at 8:46 on a tuesday”), but it doesn’t change her stance on me or us. I outright ask if she’d like to try again and she outright says no thank you, but in different words.

This hurts in a secondary way I hadn’t anticipated.

3 p.m. Today I’m busted open, entirely and completely, for the second time in three days. It fucking sucks, man.

6:09 p.m. O comes over and we get a drink at the bar you can spot from my bedroom window. I’m sad, but I hide it well, and we have rough sex with lots of choking and ass-spanking, but all I can see is the face of the girl who rejected me.

10:06 p.m. O leaves and I channel the misery into my horror story. Not the one I’m writing, the one I’m living. Things will get better. Or they won’t. In a weird way I feel a special thrill to be feeling this raw hurt. It’s a privilege, I try to tell myself, to meet all the people I’ll meet in my life.

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