sex diaries

The Graphic Designer Who Won’t Have Sex Until the Third Date

Photo-Illustration: James Gallagher

This week, a woman who tried to quit dating apps but couldn’t stay off for long: 25, single, Brooklyn. 


6:15 a.m. I wake up an hour before my alarm goes off. I spend half an hour trying to fall back asleep before I give up and take a vibrator out of my bedside table and masturbate. I have four vibrators, but only the clunkiest, cheapest one seems to do the trick.

7:30 a.m. I do a workout class over Zoom. One thing I’ve appreciated while working from home is using the 45 minutes I used to spend commuting to exercise. Working out in the morning does wonders for my mood.

9 a.m. After a quick shower, I make breakfast and sit down for work. I’m a graphic designer, and I’ve been working from home for over a year now. For the most part, I love working from home, but I’ve reached a point where I’d like to go to the office at least once a week for the sake of getting out of the apartment.

1 p.m. I drag myself up from my computer to have leftover pizza for lunch before going back to my desk. I have dinner plans tonight, so I’m trying to grind through everything due at the end of the day so I can log off right at six.

6:30 p.m. I hop on the train and meet two of my friends from work, Becca and Jordan, on the Lower East Side for dinner. Becca has just moved back to the city after a year of working remotely at her parents’ house, and it’s the first time the three of us are hanging out together since last March. Becca asks about my dating life, and I fill her in on the same story Jordan has already heard me rant about for the past month.

I just got back into dating several months ago after a two-year period I jokingly refer to as my “voluntary celibacy.” After I graduated from college, I decided to take some time off from dating to get my mental health back on track and start my first full-time job. Once I felt ready to date again, the pandemic hit.

It took two months of shitty dates to find someone I really liked: a supercute, successful lawyer. We met on Raya. After our second date, I went back to his place. The hookup was amazing. We didn’t have sex, but he made me come fingering me.

He was in between apartments and left the city for a month between our second and third dates, which gave me a month to obsess over him. He was smart, witty, cultured, and well traveled.

I slept over after our third date and left the next morning with a bad feeling in my gut. I reached out a week later, and he told me he was “looking for something serious” and “didn’t see us heading in that direction.” I think that guys think I make a fun, brief fling but don’t think of me as someone to be taken seriously enough to pursue a relationship with.

I tell my friends that I feel absolutely insane for still being hung up on this guy a month later, nevertheless someone I only went on three dates with, but it was the first taste of mutual attraction I’d had in two years, and it made me realize how badly I want to be in a relationship. I mull over all the things I did wrong … My friends tell me I’m being too hard on myself.

8:30 p.m. After dinner, my friends and I walk to another bar to get a few more drinks. Jordan tells us about her boyfriend, whom she met on Hinge seven months ago. Becca tells us that her manager met her boyfriend on Bumble. I feel down hearing about all the people I know who have found love on dating apps when I haven’t had any luck.


7:30 a.m. I drag myself out of bed and sit down for work.

3:30 p.m. Email out my last brief due EOD and hop on the uptown L train. My team takes half-days on Fridays, and since fitness studios reopened, I’ve started using them to go into the city to take a HIIT class.

4:30 p.m. I head home and debate whether to text a guy named Cory I met on Bumble back in March. We went on our second date about three weeks ago, and when he stopped texting afterward, I thought he had ghosted me. I gave it one last shot a few days ago and texted him. Now he and I are supposed to get dinner tonight, but it’s almost five and I still haven’t heard from him.

6 p.m. I text Cory, and he asks me to reschedule to tomorrow night. I begrudgingly agree. He’s super-apologetic and says that pizza’s on him in return for how patient I’ve been with him and his “terrible scheduling/texting routine.”

8:55 p.m. One of my best friends from high school and her boyfriend just moved to the neighborhood a few weeks ago. I go to their place for a few glasses of wine.


8 a.m. I snooze my alarm twice before getting out of bed to head to McCarren Park. I joined a running club two weeks ago after my mom, my brother, and my therapist each told me that I needed to pick up some hobbies so I would have more to focus on outside of work than dating. I meet the group to run a 3K around the track, and I trail behind everyone else. I’ve been running on a treadmill for years and had no idea how different running track would be.

11 a.m. My friend Ty texts me and asks if I want to meet up. We met when we lived together in college, and we’ve been close since. We meet for coffee by the park, and they fill me in on their Friday night. They just entered a serious relationship a month or so ago and spent the night hanging out with their boyfriend and his friends. Ty has never had any problems dating, and I’ve always been jealous of the relative ease they seem to have attracting men and maintaining relationships.

5 p.m. I go home to shower and take a nap and then wake up at 6:30 and check if Cory has texted me. We’re supposed to meet in an hour. I text him and ask if we’re still on, and he says he’ll be heading out in 20 minutes.

7:30 p.m. We meet for pizza and drinks before getting back to my apartment around 9:30. We each have a glass of wine on my roof before heading downstairs.

9 p.m. Back in my room, my dog starts snoring while Cory is going down on me; I have to interrupt him to kick my dog out of the room. That’s as far as we go, but it lasts for a long time.


6:45 a.m. Cory and I wake up, have sex, and then doze intermittently for the next few hours.

9:45 a.m. He heads out and tells me he’ll text me, but after our on-off communication the past couple of weeks, I know I can’t count on it. He’s really sweet and we seem to click really well, and I’ll see him again if he does reach out. But if he doesn’t, I’ll let it go.

12 p.m. I opt out of the Zoom workout class I had signed up for and swipe through Hinge for a bit before taking a nap.

3:17 p.m. I am, admittedly, bummed that Cory hasn’t texted me.

7:12 p.m. My friend invites me over to her place for dinner. She thinks I want a guy to want me more than I actually like him. She’s right. I head home after a few hours and fall asleep early.


7 a.m. I forgot to change my alarm today so that I could sleep in. I lie in bed for 30 minutes, and when I still haven’t dozed back off, I decide to get up and run to the gym.

9 a.m. My to-do list today is crazy. I put my phone in a drawer to try to keep myself off it. Both of my roommates are at the office today, so I get to blast my music while I work.

12:43 p.m. I get up for lunch and pull my phone out of the drawer to check my texts. A guy named Leo who I gave my number to on Hinge a few weeks ago texted me. I go back to look at his profile — he’s cute!

6:28 p.m. I talk to my older brother on the phone. He and his girlfriend just broke up on Saturday, and he asks for my perspective. From the sound of it, she has a lot going on right now, and it doesn’t have much to do with him. I try to take note of this looking back on the past month’s events and going forward.

9 p.m. Leo and I make plans to get drinks on Wednesday night.


5:55 a.m. My alarm goes off, and I lie in bed for 20 minutes and consider skipping 7 a.m. practice with my new running club. I skip putting on makeup before heading to the L. When I get there, I beeline straight to the slowest-pace group.

9:15 a.m. I’m going to the office today for the first time in over a year to pick up some samples and film content for my company’s website.

6 p.m. I get drinks with some colleagues at a bar nearby before walking to Chelsea for dinner. I fill them in on my recent dates. At 25, having never been in a serious relationship before, I worry men just don’t see me as real life-partner material. But I’m probably getting ahead of myself.

8:30 p.m. I get home and see that my watch says I ran 4.29 miles this morning and walked a further 5.5 throughout the day. I swipe through Hinge and scroll through Instagram for an hour before passing out.


6:55 a.m. Wake up and go for a run. My calves are killing me after yesterday, but I’m trying to improve my pace after Saturday’s embarrassing 3K.

12:30 p.m. It’s almost 80 degrees today, so I take a break from work to take my dog to a nearby dog run after I eat lunch.

6:15 p.m. I meet the Hinge guy, Leo, at a restaurant nearby. He’s a little fratty, but he’s also a designer, and it’s nice to talk to someone with similar interests. After burgers and a bottle of wine, we walk to the park and make out. He lives nearby and invites me over.

9 p.m. Now I have a hard “no sex until the third date” rule with anyone I see myself wanting to date seriously. I’ve had too many guys I’ve really liked check out as soon as we have sex. I’m not sure yet if I see this guy as a future boyfriend or not, and after half a bottle of wine, I’m easily persuaded. We do just about everything besides actually having sex.

11 p.m. He asks if I want to sleep over, but it’s a work night so I get an Uber. I think about my life on the ride home. I’m trying to start having more fun. I want to be okay with some guys just being fun hookups and nothing more. But I do hope I find someone who could be a boyfriend along the way.

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The Graphic Designer Who Won’t Have Sex Until the Third Date