The Man Who’s Intimidated by the Women He’s Meeting on the Apps

Photo-Illustration: Marylu Herrera

In this week’s story, a young architect starts a new job, and possibly a new relationship: 25, single, New York. 

DAY ONE

8 a.m. It’s my first day at a new job, and my first week living on my own in New York. I’m starting on the lowest level at this architecture firm, but after many years of grad school, I love that I can  finally call myself a working architect. This puts a spring in my step.

9 a.m. I got very lucky and scored an apartment that’s walking distance from the office. It’s the smallest studio you can possibly imagine, but the building is clean and the rest is doable: My entire paycheck covers the monthly rent and utilities, with not a penny left over, but at least I have shelter.

1 p.m. First days are always scary, but everyone here is very welcoming. My desk is in a converted supply closet. The thing about being an architect at a sexy firm is that it’s actually very unglamorous work.

2 p.m. Finally duck out of the office to go grab some Shake Shack. My parents give me $1,000 a month so I can actually eat. They are both architects too, and I grew up in a rent-stabilized apartment on the Upper West Side. My parents are still there, but I wanted to finally live on my own.

While I’m sucking down my burger and fries, I go on the dating apps. I’m newly single. I had the same girlfriend in high school and college, and three months ago, she dumped me and came out as a lesbian. It’s not great for the ego, but I’m determined to make peace with it. I loved her a lot. I was heartbroken. With the new job starting, and the move from Vermont — where we were living — I’m basically entering my new life right now.

5 p.m. I get a message from Victoria on Hinge. She asks me if I’m interested in casual sex and if I have a big dick. I’m only 25, and I feel intimidated by how sexually open and aggressive everyone is. I’m honestly afraid of her, so I’m not writing back.

8 p.m. I’m the last to leave the office. My parents told me to try to be the first to arrive and last to go, every day, and today I accomplished both. I had a good first day, but I’m drained.

10 p.m. I smoke a joint and listen to music while setting up my little studio. I make a note that I need a plant and wineglasses. Then I jerk off to internet porn and go to bed.

DAY TWO

9 a.m. At the office. I was smarter today and remembered to buy a coffee and a big breakfast on the way to work. So I’m sitting at my desk inhaling both right now.

10 a.m. There’s a lull before the morning meeting, so I quickly look at the dating apps. I see someone named Katie who seems just my type. Fun, sweet, “normal.” I like sex, but I’m not driven by it like a lot of guys. I’m more interested in an emotional connection than getting laid. I mention that because everything online feels so sexualized, and I like that Katie seems somewhat wholesome. I ask her if she wants to go out tomorrow and she quickly says, “Yes! Where?” Shit. I’ve been living in Vermont for three years; I don’t know what’s cool.

1 p.m. I ask my older sister, Ella, where to take Katie that’s fun but super-cheap. I can’t really spend more than $60. She tells me about a bar on the Lower East Side that has free chips on the table but is also cool and socially acceptable. Then she Venmos me $50. Ella’s a corporate lawyer. And my whole family has felt really bad for me since my girlfriend dumped me, so they’re babying me a little bit. I can’t complain.

6:45 p.m. I meet a few friends from graduate school at a bar in Brooklyn. I try to seem cool, but honestly I have no idea where I am and I’m calculating how much my second drink will cost the entire time.

9 p.m. Lucky for me, a trust-fund kid who I don’t really like picked up the bill. He’s a prick and a misogynist who struck out with every girl he flirted with, but I can’t be mad about it. A random girl there was flirting with me, but I just wasn’t into it.

11 p.m. I’m a little bit drunk, and I’m sad that my girlfriend is gone, but I try to feel excited about my date with Katie tomorrow. Maybe we’ll fall in love. I’m a girlfriend guy, what can I say? I jerk off while sitting on the toilet, because it’s almost no different from brushing my teeth — just part of my nightly self-care routine. I think about having sex with a hot anonymous girl and come in less than a minute.

DAY THREE

8 a.m. Feeling more excited about my date tonight. I call my parents on the way to work: they’re my biggest champions. I tell them I have a date tonight, and when we hang up the phone, they Venmo me another 50 bucks. Wow, I must seem super-pathetic to everyone I’m related to. I feel rich.

10 a.m. I have my first client meeting today. My only real job is to take notes and pay attention and be charming. I think I do a good job.

1 p.m. I text Katie about the plans for tonight. She hearts my text. It gives me a stiffie, which I hide by not leaving my office for a half hour.

4 p.m. There’s a female architect here, Claire, who keeps telling me I’m handsome. Like, when we pass each other in the office, she says, “What is like to be 25 and so fucking hot?” I just blush and walk away. I like it, kinda, but I wonder if it’s sexual harassment. I don’t really care, but it’s slightly uncomfortable. She is a MILF, for what it’s worth.

7 p.m. I walk home to shower and change before my date. She texts that she’s leaving work and should be there soon. She’s a fashion publicist, which turns me on. I’m so basic.

8 p.m. Katie is cute, but I can tell she’s not my next girlfriend. She’s too crass, too loud, too wannabe Samantha from Sex and the City (I have an older sister). I decide to get drunk and try to hook up anyway. She seems like she’s looking for a good time.

10 p.m. We’ve been overserved and she’s pushing to see my little studio. She keeps saying, “The smaller the apartment, the bigger the dick.” What is with these women and penis size? I think I’m perfectly adequate in that area, but suddenly I’m feeling insecure.

10:30 p.m. We start fooling around the second we walk into my apartment. She’s aggressive. I like it. But it’s a little bit weird since I know I’ll probably never call her again. I try to stay in the moment and enjoy the physical connection and not worry about the aftermath.

11 p.m. The sex is good — she’s loud! I think she wants to sleep over, but I make up a lie and say my parents are coming early tomorrow morning. She calls me a mama’s boy (not untrue) and says I should Uber her home. I almost never use Uber because of my budget, so I hope it’s still active on my phone, and then I order one for her. She lives in Brooklyn, so it costs almost $70. I feel sick and regretful but try to stay sexy and charming.

11:30 p.m. Before she leaves, she invites me to her birthday dinner later this week. She’s turning 25, so we’re the same age. I stupidly say, “Totally!” I’ll try to undo that tomorrow.

DAY FOUR

10 a.m. Today, I have a moral hangover, not an alcoholic one. Was the sex good? Yes. But can I bring myself to see Katie again? That’s the bigger question.

Noon Text from Katie with details about her party. There’s going to be an open bar and food trucks with free tacos outside the venue. I think she might be rich. I text my buddy Tyler to see if he wants to join. What’s one more face-to-face session with her?

4 p.m. One of the partners here asks if I want to grab a drink after work with a few of them, including the MILF. I feel nervous about sounding young and dumb in front of them, but obviously I have to say yes.

6 p.m. We all pack up to leave the office. I feel like I’m playing “architect.” We go to a bar down the street. It’s fancy. Everyone orders dirty martinis, so I do the same. The MILF is sitting next to me.

After two drinks, everyone is sharing about their personal lives. I’m basically the only unmarried one, and I think they all have kids besides me. They want to know about dating apps. They’re practically drooling when I tell them about how straightforward people are about what they like, sexually, online. I show them a screenshot from a girl who asked me if she could bark like a dog at my bedside. Then I start worrying I should have kept that to myself. The MILF is semi-flirting, but it comes out that her husband is literally the most successful architect in the city, so I make a promise to myself that I will never be tempted by her.

10 p.m. When I get home, I have multiple texts from Katie asking me to come over. The martinis made me horny, but I don’t want to give her false hope. I’ll go to her party tomorrow, but that’s it for us.

DAY FIVE

9 a.m. I’ve never said “TGIF” before, but TGIF. It’s tiring being an adult.

10 a.m. Tyler’s in for tonight. He suggests a few other friends we should invite. I text Katie asking if I’m allowed to invite more guys. She replies that they can come if they’re (1) hot and (2) single. I tell her that I think they check both boxes, but honestly I have no idea. One is pretty short, but “short kings” are in, right?

2 p.m. My direct boss comes into my office to tell me I did a good job this week. No notes! I feel happy. I text my parents and sister and tell them I got a great report.

4 p.m. Katie texts and asks what I’m getting her for her birthday. Is she joking? I didn’t plan on getting her anything and I have no extra income. I have a gut feeling that I shouldn’t go tonight, but now I’m traveling with a crew of five guys, and they’re stoked.

7 p.m. Walking home from work, I debrief with my sister. Ella says Katie sounds like a psycho, but that it’s all part of the New York experience, and I should have an open mind.

9 p.m. We pregame at my buddy’s apartment. He’s in finance, and so are his friends. Katie’s crew will be excited, though; everyone is pretty good-looking.

10 p.m. We show up at the party. Katie gives me a huge hug and a kiss on the cheek. She looks great. I decide to have fun and not worry about leading her on.

1 a.m. After hours of drinking and dancing — this party is epic — Katie is throwing up and her friends are getting her in an Uber home. I’m not mad at all that we didn’t go home and hook up. We did grind on the dance floor for a while. I didn’t end up getting her a present, and she never mentioned it.

I share an Uber home with some friends because I’m too scared to take the subway this late at night.

DAY SIX

9 a.m. Okay, today I have a real hangover. I try to hit the gym to sweat it out, but I end up only staying for 30 minutes. My head hurts.

Noon I make a couple grilled cheese sandwiches and drink as much water as I can. Then I lie on the couch and watch TV and do nothing for hours.

4 p.m. Katie texts me something short and sweet about being embarrassed how the night ended. Maybe she’s not a psycho. I don’t want her to feel embarrassed. She (or rather her parents, I suspect) threw a tremendous party! I tell her that. We make plans for tomorrow night. I’ll give it one more shot.

8 p.m. I meet my sister and her boyfriend for sushi — she pays — and we just relax and enjoy the night. I’m so thankful for her.

9:30 p.m. She walks me home and checks out my studio, then orders me a few things on her Amazon account — cleaning supplies, mostly — and leaves. I feel happy and safe knowing she’s only a 20-minute walk away. She does warn me to avoid Katie; she thinks she’s a stage-four clinger.

DAY SEVEN

10 a.m. I’m inspired to make my apartment look spiffy today. I go to a thrift shop and buy a few things for cheap, like a chips-and-salsa bowl for 50 cents.

11 a.m. Katie wants to have brunch. That sounds expensive. I suggest movie night instead. I’m curious to see her place, and when she invites me over, it feels like the right move.

3 p.m. I spend money I shouldn’t on flowers to bring Katie. I know she’ll like that, and since I didn’t get her anything for her birthday, it feels too awkward showing up empty-handed.

6 p.m. Katie’s apartment is beautiful. It’s small but so fancy. The ceilings are high, the kitchen is nice, she has a couch that I know for a fact cost almost $10,000 (I’m a design nerd, and I know the brand and the fabric). I’m like, “How do you afford this?” She says her parents pay for her lifestyle, which I honestly find to be a bit of a boner killer.

7 p.m. We’re drinking wine and talking at her kitchen table. She’s getting a little vulnerable and telling me about some romantic traumas in her past. I’m trying to be a good listener, but it’s kind of an eye roll. Her life has been pretty perfect — not that mine hasn’t. All I can think about is how much more wine do we have to drink before we can fuck.

9 p.m. Still not having sex. I tell her I’m going to “call it a night.” She says, “Not so fast!” She straddles me on the kitchen chair I’m sitting on and we start fooling around. She’s putting her boobs in my mouth. She tells me to call her a “slut,” and I tell her I won’t do that. Nevertheless, we move to her bedroom. It’s so clean and crisp. We have sex. It feels amazing, but deep down, I just want to come and leave.

10 p.m. So that’s what I do. And I decide that’s the last time I’m going to see Katie again. I tried!

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