sex diaries

This Week’s Sex Diary: The Woman Whose Mom Sends Her Money to Join a Dating App

Photo-Illustration: by Marylu Herrera

In this week’s story, a woman sleeps with her ex’s best friend and goes on dating apps for the first time: 29, single, New York.


8:20 a.m. I wake up feeling anxious. I hate when I get like this. I made a big mistake last night.

9 a.m. After a nice long shower, I’m feeling a little better. I have a lot going on right now. I’ll give you the short version: About a month ago, I broke up with my fiancé. I wasn’t in love with him, and I feel like if we were married, we would have been divorced pretty soon. But it’s been rough. I’ve been drinking too much and partying too hard. And last night, I made my worst decision yet: I slept with my ex’s best friend from college.

10 a.m. At my office. I work for a media company in ad sales. My head hurts. It’s from the martinis last night. Against my better judgment, I text T, the guy from last night: “What were we thinking?”

11 a.m. Crickets.

3 p.m. I try to focus on work. I’m taking some clients to a basketball game this week. I also have about 300 emails a day to respond to. I get going on some of them and try to ignore my pounding head.

5 p.m. On the subway home. I just want to bawl my eyes out. What am I doing with my life?

7 p.m. At home feeling awful. My ex and most of his friends hate me for calling things off. My family is loving and supportive, but I put them in a really bad spot financially — they had already put down money for the wedding. And now I’ve fucked T and he’s ghosting me. He’s a classic New York banker asshole, but I was drunk, and we’d always had sexual tension, and I guess we’re both complete trash bags. If he tells my ex what happened, I don’t even know how bad it will be. Then again, how much worse can it get?

9 p.m. I take a sleeping pill and go to bed.


6:30 a.m. I’m up early, so I decide to go to the gym and try to have a healthy day.

8:30 a.m. Showering for work and my anxiety starts to seep back in. Why wouldn’t T text me back? It just makes me wonder if he told my ex everything. I start to feel paranoid and wonder if my ex and his friends would actually try to ruin my life. I don’t know — could they get me fired? Put me on blast on social media? I know I’m being crazy, but I can only imagine the worst right now.

9 a.m. I text T again: “We don’t need to meet up ever again, but please tell me why you’re ignoring me?”

1 p.m. At work. I have one very close friend here, who knows all about my ex-fiancé. Over lunch, I tell her everything about my night with T. She asks more about the sex. Honestly, it was pretty wild — like porno wild. Rough, dirty, hot. A million different positions. I enjoyed it. Sex with my ex was so boring. Our whole relationship was boring. And like I said, I’ve had a vibe with T since I met him. He’s a self-proclaimed dirtbag, and I think deep down we both knew it would happen at some point.

5 p.m. It is fucking absurd that T has not texted me back. My anxiety is through the roof.

7 p.m. I take a hot-yoga class. It helps. For a minute.

10 p.m. Sleeping pill and bed.


9 a.m. I have such a long workday today. That’s a good thing — it will keep me from thinking about T and the mess that is my life.

11 a.m. At work. Just completed the first of three back-to-back Zoom meetings.

3 p.m. I’m Zoomed out and starving. I run to grab lunch at a nearby taqueria. I notice a few cute guys who must work in the neighborhood, and one of them smiles at me when he walks past. It occurs to me that I need to stop acting wild and start dating in a healthy way again. The last couple of weeks have just been so sloppy — I’ve been having random one-night stands a couple times a week. There was also one night where I tried to hook up with a girl at a party. I was wasted and when I tried to kiss her, she pushed me away. It was an intense reaction. Thinking about that night is upsetting — it was just very messy. I’m sick of the mess.

6 p.m. Client dinner. We’re at a steakhouse. I like these clients, but they’re all married with kids, so the conversation is strained for me. I don’t like to share much about my personal life with the people I work with, so when they ask questions, I’m pretty vague. I’m sure this makes me seem boring, but I don’t want to mix business with pleasure.

9 p.m. At the basketball game. Everyone is yelling and having a good time, and I realize I haven’t thought about my love life in a few hours, which is progress, I guess.

11 p.m. I’m home from dinner and the basketball game. It was fun, but it was definitely work. I pass out the second I’m in bed.


9 a.m. Another morning waking up feeling anxious. Still haven’t heard from T. I’m sure he told my ex.

11 a.m. At work. I take a walk outside to call my mom. I can tell she’s worried about me, and when I hear her voice, I just start sobbing. I tell her that I feel so lost and so lonely. It seems like no one is texting me or inviting me out. I have to start over, and I don’t know how.

My mom is comforting. She pushes me to go out and meet new people. She suggests online dating, which I’ve never done before. I know that sounds crazy for my generation, but I met my ex in my early 20s at a bar and I just haven’t been single since then. My mom then sends me $100 on Venmo to join a dating app. My parents don’t have a lot of money, so this makes me cry even harder. I promise to download Bumble.

4 p.m. My boss tells me that I’ve been doing a good job and hints at a promotion. It feels great to hear, but then I get sad, because I feel like I have no one to share the news with. Well, there is Mom. I text her and she’s thrilled.

8 p.m. Home with a glass of wine. I download a few dating apps. It’s kind of fun, but it takes me a long time to fill out all of the info and pick photos for my profiles. I decide not to do any swiping until tomorrow.

10 p.m. My friend from work gave me a vibrator when I canceled my engagement, so I decide to use it tonight. I set up a whole scene: a candle, nice silk pajamas. Then I lie down and realize the damn thing needs to be charged! I guess we’ll wait until tomorrow …


9 a.m. I see my friend in the elevator at work and tell her about my failed attempt to use her gift. We have a little laugh. I feel lighter today.

11 a.m. In the bathroom, feeling anxious. I take a second to spiral about T — that he fucked me, never contacted me again, and that he probably told my ex everything. Then I push the thoughts away. I’m going to try to stay positive …

4 p.m. I run out of work early to take a spin class. I am turning a corner and trying to take better care of myself. Starting, like, now.

7 p.m. Home, showered, ready for a quiet weekend in …

8 p.m. Of course, this is when I get a text from T. Why does the universe work this way? The text says, “I feel disgusted about what we did. I think it’s better if we cut all ties. Thank you for respecting my boundaries.” Whoa. What the actual fuck. I honestly don’t know what to think.

11 p.m. I do not text him back. I guess a small part of me is relieved that he wrote something — anything — back. But what a fucking dick. “Disgusted” is a pretty strong word. I go to bed hurt and offended.


6:30 a.m. I couldn’t sleep. I was tossing and turning all night. It’s Saturday, so I decide to stay in bed and get some more sleep.

8 a.m. I very rarely smoke weed, but I smoke a little this morning because it tends to make me sleepy.

1 p.m. It worked! I just woke up. I force myself not to think about that awful text. Instead, I make a strong pot of coffee and start swiping online. I promised my mom, after all!

7 p.m. I’ve been swiping and chatting to guys for six hours. Six hours! I realize that I’m starving. I order a lot of Chinese food.

8 p.m. Eating and watching a movie. I set up three dates for tomorrow, but my fingers literally can’t swipe or text anymore, so I’ll deal with the logistics in the morning.


9 a.m. Another spin class. I can’t believe I have so many dates today. I need to cancel on a couple. I know it’s bad form, but I’m new to this and still fragile.

11 a.m. After class, I review my dates. I decide to keep one with this guy named Max. I’m transparent with the other two: I tell them that I’m very green with this stuff and I overbooked myself, but that I’d love to reschedule. Both say it’s totally fine!

4 p.m. Max suggests we get margaritas and tacos, which is my idea of the perfect Sunday night. I’m excited to meet him. I text my mom that I have a date, and that he seems very sweet. He’s a high-school teacher, he went to a good college, and he seems earnest and enthusiastic. Mom is excited for me.

7 p.m. We walk into the restaurant at the same time. At first glance, I can tell that Max is super nice, and that we should be friends, but I’m not attracted to him. It’s okay!

9 p.m. The date is over. I had a lovely time. It felt comfortable and nice, and Max was so cool, even when I spilled my guts about what the last few months have looked like for me. I don’t think he was into me romantically either — I’m sure I came off as a hot mess. But overall, it was a cathartic experience. Maybe this won’t be so bad?

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The Woman Whose Mom Sends Her Money to Join a Dating App