sex diaries

The Woman Getting Late-Night Texts From an Old Fling

Photo-Illustration: James Gallagher

This week, a woman who’s recently sworn off dating decides to meet up with a man she hasn’t seen in years: 35, single, Los Angeles.


9:00 a.m. Wake up and start cleaning the house. I somehow wash the pile of dishes in the kitchen sink without actually making any change in the ratio of clean to dirty dishes.

12:00 p.m. Go on one of my twice-weekly long pandemic walks where I get lost in neighborhoods among bougie houses and manicured succulent gardens. The canyons and Hollywood Hills offer a whole labyrinth of winding roads and hidden staircases.

5:00 p.m. Back at home I listen to a podcast while making dinner. It’s a nice end to a relaxing day and I go to bed early.

10:30 p.m. I wake up because my “rainstorm” white-noise app has halted unexpectedly. I roll over to start it again and see a text from an unknown number, Pacific Northwest area code. It’s about the Smurfs. The message feels familiar and the sender appears to know me. I’ll deal with this tomorrow.

11:00 p.m. No luck falling back asleep. My feelings-brain needs rest, my thinking-brain needs to know who this is. I get to work: I don’t just reopen Tinder and Hinge and OkCupid, I have to reactivate my profiles. Like anyone who dates, I recently swore off online apps in the name of exhaustion, terrible sex, ghosting, and well, the pandemic. My search is focused on matching the phone number to a message, likely from a while ago. I scroll and scroll and scroll, going way back. There he is. It’s Alex, who I went on a few dates with two years ago. Satisfied, I put my phone away and turn over, planning to investigate this in the morning.


6:20 a.m. I wake up thinking about Alex. He was a gangly, awkward tech bro who cheerfully loomed over me at six-five. A full-fledged dork and smart as shit. I liked him and his shock of black hair. Although he wasn’t a good kisser, I find myself reminiscing about him anyway. (This is some late-stage pandemic shit: replaying bad dating memories just to feel something, anything.)

Last summer and fall I went balls to the wall, squeezing in as many dates as I could while maintaining social distancing. After a two-month mini-relationship ended in October, I consciously stopped dating for a few months. But the new year brought on renewed engagement — the last date I went on was about two weeks ago. It was with a man who occupied 85 percent of the airspace talking about his music and roommates. I haven’t seen him since.

10:45 a.m. Do I respond to Alex? What is happening? Does he want to have sex? Ugh, I’m not in the mood to entertain this.

1:00 p.m. I break for lunch. I work for a generous and surprisingly well-organized literary nonprofit. I am so lucky to have this WFH job, even though my grant funding expires soon and looking for a new gig during the pandemic is less than ideal.

5:45 p.m. His text stares up at me. Okay, fine. I respond: “Hey there! How are ya?” Am I informal enough? What tone do I use to ensure sex is not on the table? 

6:00 p.m. Of course Alex responds immediately. He sends several emoji and wants to know what I’ve been up to, then asks me on a hike. To be fair, I also ask friends to go on socially distanced hikes and he’s not actually the first ex to make this request. Wait, is he my “ex”? We had three dates. The sex occurred on the third date. There was not a fourth.


3:15 a.m. I wake up in a sweat, reaching for my kitty who always sleeps curled in one of my nooks. He’s not there. I collapse in tears — it’s been two weeks since he passed. For 11 years he was my greatest love.

7:00 a.m. I sleep a bit after calming down. I’m told gratitude is the way through grief but for now it’s just inextricable sadness. Tomorrow is meant to be the hiking day with Alex. I text him to ask for a rain check. I’m in a state. He understands.

10:00 a.m. I visit my friend Carlos, who’s become my quarantine BFF since he lives right around the corner. He makes coffee that we eat with slightly stale conchas. We actually met the very first week I moved to L.A., when we went on an OKCupid date. We had a nice time, but decided to just be friends. Now we see each other weekly for outdoor, socially distanced coffee or meals on his patio where we talk about everything: dating, writing, creative projects, his music, ideas for a podcast, etc. I’m so grateful for him.

12:00 p.m. I edit a spreadsheet containing book metadata. I’m having an intellectually unplugged day and this is a task I can do well in that mindset.

5:00 p.m. I cook to distract myself, roasting butternut squash and other vegetables to make soup. I always feel very proud when I make something delicious.

8:45 p.m. I’m thinking about this past year of dating, and what I want from a relationship. I was divorced at 28, which sometimes makes me feel like I have a bit more experience than most people. We’d met in a restaurant. He was my server, and I left him my phone number on the receipt with a horrifyingly embarrassing note. As time went on, I could see our paths diverging further apart. Now he lives on a farm in rural Oklahoma with dozens of chickens, dogs and cats, and a deer.

9:00 p.m. If we do the hike, I will have to make sure there’s no innuendo perceived on his part. I can’t deal with my memories and feelings. I’m going to melatonin- and CBD-infused sleep.


8 a.m. Zoom call with my colleagues. They’re on the East Coast so I often have meetings at earlier-than-normal work hours. I didn’t mind it because I’m an early riser. It’s such a kind, supportive work environment and I always feel like a jerk with my sunny, palm tree–laden background while it’s frigidly cold and rainy in New York.

12:00 p.m. Spend my lunch break watching a Great British Baking Show episode because I’m hooked.

2:30 p.m. I realize I haven’t thought about Alex all day when he texts to check in. I feel sorta guilty; maybe being outside under sunny California skies with another person is exactly what I need right now.

7:45 p.m. We’ve spent the evening texting. It’s not the witty repartee I remember from our “relationship” but I guess there’s no pressure this time around. “I’m looking forward to seeing you! You’re so pretty, I loved your hair.” He’s being nice. But please God don’t let this be some kind of pre-hike foreplay.

9:15 p.m. I toss the phone on my bed to snap myself out of this. I gotta clean the kitchen and feed my sourdough starter.


12:15 p.m. We decide to meet up this weekend. We’ll hike, we’ll chat. It’ll be great and very normal. But now that we’ve got the meeting scheduled again, the timbre of our conversation shifts. He’s dropping memory pins of our time spent naked together. Why, Alex, why. “I remember how big your breasts were,” he messages. “Not relevant!” I reply.

I’m beginning to regret making these plans. On the fateful — and final — date No. 3 we made soup together at his house. It was awkward, and I could feel how badly he wanted to have sex. After dinner, we retired to his bedroom, where he started giving me the weirdest, wettest kisses I’ve ever received. The sex wasn’t any better — he asked to do missionary, and stiffly positioned himself over me, encaging my entire body without so much as a skin cell touching mine.

12:50 p.m. He asks if I remember cooking with him. “It was so fun!” he recalls.

4:00 p.m. I go to the market to stock up, and decide I’ll make salmon cakes over salad for dinner.

6:00 p.m. I’m late to the pandemic baking trend (GBBO helped) and this evening I’m making yeast cinnamon rolls. Carlos is frequently the recipient of whatever baked good I’m making for the week.

8:00 p.m. I spend the evening thinking about whether or not I actually want to meet up with Alex. Especially after the breast comment, I feel like I have the right to withdraw. Then again, pandemic isolation convinces me otherwise.


8:00 a.m. It’s Friday! I make a whole French press’s worth of coffee with locally roasted beans. It’s my special treat. I do calisthenics on my yoga mat while waiting for the water to boil.

10 a.m. I edit a friend’s grant application and am, as always, extremely impressed by the highly capable people I know.

3:15 p.m. My best friend and I text, trying to figure out when we’ll have our wine-date Zoom to catch each other up on the monotony of our lives. I tell her Alex has resurfaced. “LOL. It’s pandemic times though,” she reminds me. She chortles but says that everyone’s just looking for a connection. Yes, yes, she’s right. But doesn’t she remember the terrible sex I told her about?

9:40 p.m. He just texted to confirm tomorrow. There’s no backing out now. Get it together! It’ll be fun. Stop overthinking.


9:00 a.m. It’s hike day. Our plan is to meet in Griffith Park. I saddle up my water bottle and little daypack. I’ve packed snacks, hella snacks. This is like a three-mile hike, but listen. You can never have too many snacks.

10:03 a.m. As I’m parallel-parking near the trailhead I feel a hot flash coming on. What if he wants to fuck behind a cactus? Have I given him the wrong impression? How careful is he being about COVID? I sit for a second in my car, preparing for the “break-up” conversation, if I have to politely escape.

10:53 a.m. So far so good! Pretty views, intelligent conversation. I remind myself why I tried to make it work while also simultaneously knowing why it didn’t.

11:03 a.m. He starts making more innuendos. I’m wearing a T-shirt and long-sleeve lightweight hoodie. It’s pretty warm out, but I’m comfortable. “You know, I’ve seen it all before,” he says. “You can take your shirt off.” I’m tongue-tied. Does he think I’m going to walk around this public park in my bra? Or topless?!

12:30 p.m. Post-hike he asks me to grab coffee and hang out on a bench outside. I tepidly agree. As I sit down, my aging back catches and I tense up. “You know what you need, a back massage!” he says with a wink. I decline his offer.

The day after our third date, I had broken it off with Alex with one of my patented I-liked-getting-to-know-you-but-I-don’t-feel-a-romantic-connection texts. He never responded. I feel like I’ll have to do it again.

1:00 p.m. I tell him I need to pee and should get home. (Both true.) He says next time we can do a hike closer to my house.

7:05 p.m. “It was so nice to see you, let’s do it again,” he texts. “Hope you found a toilet!”

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The Woman Getting Late-Night Texts From an Old Fling