The 28-Year-Old Partying Hard in Montauk

Illustrated by: Marylu E. Herrera

This week, a marketing assistant escaped on a family trip, only to realize she’d stayed too late with a potential relationship: 28, single, Long Island.


9 am Back to work after the weekend. I work in marketing at a very small company in Manhattan, where I drive from my hometown on Long Island (where I live with my mother). I wear a lot of hats and get paid super low. Basically, I’ve been trying to find a new job since I got this one.

9:40 am I got a random text from L, a guy from Bumble, who I’ve met but haven’t really connected with. “Do you work from home?” I haven’t heard from him in weeks. He’s short-tempered and a personal trainer but the things he texted me annoyed me. He kept asking me if I was using birth control, if I liked the tip, if he could fuck me without a condom? Does anyone have a feel for the decorum anymore? But what can I expect from a 23-year-old – I’m just over five, but that feels young.

I didn’t start having sex until I was 25 and still consider myself on a learning curve when it comes to dating. I’m very positive about apps but it seems guys never want to meet in person – I’ve only had two dates this summer (hence I’m 23).

11:39 am Take a break from work to test Hinge. I was recently scolded by my step sister and her friends for being too broad in age: 21-45. I thought I was opening myself up to more possibilities, but I realized I was making it harder to find people I’d actually date. So I narrowed my range down to 27-40, and now my matches are really getting better. Maybe I’ll have sex again soon!

2:20 pm Thinking of B, the last person I dated, in my youth. Another 23 years old. I fell for him on our first date but it got weird and intense really quickly. He tried to tell me he loved me three days after meeting him… during sex. And I’m just going with it for another two months despite the obvious red flags. He stopped answering one day, until texted me a week later from a new number to tell me we shouldn’t be dating anymore. Since then, I’ve been self-reflecting a lot to try to be the best “me” I can be, for myself, the people I love, and whoever I end up with.

4:40 pm Leave work to go home.

5 p.m L texted and said he was at my house. He’d never showed up before without asking, and I wasn’t sure what to do. I told him I wouldn’t be back for at least 40 minutes. He was irritable, so I told him to go home. As I approached 30, I became less and less patient with this kind of stupidity.

9 pm Lie down and fall asleep.


9:17 am Back to work. Why am I in such a bad mood? I try to think of what I can eat for lunch afterwards – it’s always my favorite part of the day, next to my morning coffee.

12:30 pm I recently got my medical marijuana card and I love the easy access to ephemeral potions. I allow myself to take 5mg before I leave work for a walk and lunch – minestrone soup and Caesar salad.

6 pm From work, I go to a yoga class. My studio has been my saving grace. It’s one of the few places where I feel real peace. The mistress at the top of her classes is so charming, I would join her cult if she had one.

8pm My friends come, we drink pumpkin beer, I feel full and we watch From dusk until dawn. Damn, Salma Hayek has been a bitch for too long.


7:30 am Ugh, drinking made me very sluggish the next day. I desperately wanted to go back to sleep, but I got out of bed and put on my pants for the first time in four months, since I really felt the chills.

11 a.m At the office. Work was slow this week, so I watched ’90s cartoons over and over at my desk. I didn’t even know what to look at with all the options so I used to nostalgic. I’ve been trying to plan my 29th birthday, but it’s easy to get overwhelmed by the choices. Maybe I should book a hotel room and see where the night takes me and who actually shows up.

1:30 pm Lunch bowl and extra TV on my desk.

5 p.m I usually go to yoga tonight, but I just want to go home, sit on the couch and watch Morning.

9 pm In bed with my familiar lullaby: Forensic records. Feel more comfortable knowing I’ll be working from home tomorrow and won’t have to spend hours in traffic.


7:30 am I was half awake and half asleep when my mother yelled “I’m leaving!” Ugh, I forgot I have to take her to the mechanic before I start the day at home. I want to move out at some point, but I don’t want to live alone. I assume I am waiting for a partner to come along to move in with…

8:30 a.m We took coffee and breakfast sandwiches, which she kindly paid for, and it lifted my cranky spirits.

10:20 am I recently purchased some micro-dose psilocybin pills that I found online. They really seem to have an effect! It’s subtle, but I feel a little lighter, uplifting. At this point in my life, I am my own guinea pig, willing to try anything that might affect my mental health.

half past eleven Poppup! Everyone on Bumble is usually so hot and successful and seems out of my league. It sometimes feels like these records were set up by some Bumble lord just to deceive us. But I’ve been spending a lot more time with it lately, and actually getting some matches with men that I’m both attracted to and the one to respond to!

2 p.m Booked a room at a hotel on the Lower East Side for my upcoming birthday. I’m grateful that I decided to treat myself instead of being paralyzed by indecision.

5 p.m Come to my pharmacy after work. I quickly fell in love with one of the cashiers here, C. Last time he called me, I glanced at his badge and then looked up at him, hoping for social media. , but all I can find is his work process. This time, another very nice man put a ring on me, but I kept my eye on C. He came and helped the other guy by taking my goods and putting labels on them. This guy is so hot and kind and that makes me super nervous.

9 pm When I went to bed, I thought about C and decided that the next time I went to his store, I would actually strike up a conversation with him.

Mother’s Day

10 am It was the weekend and I was on my way to Montauk with my dad, stepmother and step sister. Driving will be about 2 hours. I don’t want to sound ungrateful with a paid vacation, but sometimes I wish I had a romantic partner with me instead of my parents. At least my step sister is here to fix things.

2:50 pm We settled into the hotel and I was sitting on the beach with my book. I love it here, even in the fall.

4 pm Stepsister brings white wine to Pregame; I was buzzing before dinner.

7:30 pm Our early family dinner is over, I’m already feeling engrossed enough on the rosé cake and ready to go out. My step-sister is 27 years old and recently single – she’s having a lot of fun outings. I’m jealous, but I very much hope to have an evening out with her.

10 give me We were at a popular local dive bar. I like the vibe here. We went to a table with two people and started talking to them. For some reason, I immediately began to feel insecure and unwanted. My step sister can easily talk to these men while I feel like an idiot. She eventually finds out that these guys know her ex (Long Island is a small world I guess) and loses interest.

But she immediately found a new guy to look at. I’m getting drunk and really don’t want to have idle chats with this guy and his “cousin”. Then she told me they had a can of coke which I dared her to find for me and I stepped up, following them to the parking lot.

11p.m I got into my cousin’s truck with him, and he texted me some lines on his phone. I pretended to be interested in his musical taste and asked about his work, something about fishing. He’s really a nice guy, maybe I should be a little kinder to him…

1 am After a while, the four of us decided to go to the next bar. My dad texted me “Where are you?” I replied, “Coming!” The cousin invited us back to his place to hang out a bit more. I’m ready at this point, hop an Uber with them.

We end up in a messy house, where I assume one or both of these people live. I ended up working with my cousin. After that, I wanted to leave, but my step sister was talking to another man in another room, so I decided to lie on the couch for a bit.


5 a.m I woke up in a haze of smoke. My step-sister still didn’t want to leave, so I started walking back to the hotel while looking for an Uber. The little Uber icon swirled around, couldn’t find a ride, so I gave up, it seems that walking to watch the sunrise would be good. Back at the hotel, I was flipping through my contacts when my stepmother appeared in the bathroom doorway. Did I mention we’re all in the same room? I told her that my step-sister would “be back soon”, as if she were a feral cat. She turned right after me.

11 a.m Obviously I feel like hell. It wasn’t a great scene. My parents divorced when I was young, so my father was not used to waiting for me all night. I was very worried about what he would think of me or say to me.

12 pm My family wanted to go out for lunch but I desperately needed a nap, so I stayed and passed out a bit.

2 p.m God, I feel so much better. Me and my family sat on the beach.

7 pm We all went to dinner at my favorite restaurant in Montauk. It turned out to be a perfect meal with lots of laughs, and I feel grateful to be with my family.


8:30 a.m Wake up early, nice and rest to enjoy our last morning here. We sat on our deck, watched the waves, chatted and had breakfast until we decided to leave.

12:30 pm Home! I didn’t tell my mom about my runaways, because sometimes it’s nice to have things to do with myself, and I still feel embarrassed. I’m sure it will come out eventually.

4:45 pm Had the best Sunday afternoon nap of all time. There’s nothing like lying in your own bed with a warm dog by your side.

7 pm When I wasn’t minding eating, sitting on the beach, or getting drunk this weekend, I chatted with this new guy on Bumble. Now we’re finally taking the time to learn some things about each other, but he hinted that he wanted to talk about things more clearly. Call me old-fashioned, but I’d love to be taken out on a date before discussing “I’d rather give or take.” For the eleventh time in the past few years, I’m wondering if I need to take a break from dating apps altogether.

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