sex diaries

The Social-Media Manager Who Makes a Move on Her Boss

Photo-Illustration: by Marylu Herrera

This week, a woman tries to avoid thinking about her ex by going out with a guy who looks just like him: 28, single, Brooklyn. 


8 a.m. I wake up feeling refreshed for the first time in weeks. I’m coming off a really bad breakup and find it hard to sleep at night.

9 a.m. I leave the house, nice and showered, to head to work. I’m a social-media manager for a publishing house, so I always have a lot of fires to tend to. On the subway to work, I try not to think about my ex. If I go an hour without thinking about him, I congratulate myself. I open up The Guest and read a few pages until my stop.

1 p.m. My boss, Adam, and I are grabbing lunch together. There’s a chemistry between us that I’ve always been afraid to explore. We’ve worked together for three years. He hired me, and I felt it on day one of the interview process. I try to avoid thinking about it mostly because he’s my boss but also because he’s married. But my friends are all urging me to do something crazy just to stop thinking about my ex, and lately I’m wondering if flirting in a more intentional way with Adam is the answer. I have a feeling he’s in an open marriage because a friend thought she saw him on Feeld, but we’ve never discussed it. I feel ready to open Pandora’s box …

1:45 p.m. On our walk back from the sandwich place, we start talking about me dating again. I’m like, “Do you know any good guys?” My boss is like, “No one is as good as me.” We both laugh, awkwardly, and then I change the subject. Am I really ready to go there?

6 p.m. Stop at the gym on the way home. As I work out, I try to ask myself what I really want and who I really want. Do I just want some hot sex? Sex with my ex was okay but not incredible. Should I be bisexual? Should I be wild and crazy and start fucking my boss? Do I need to be alone for another few months? What should I do with my love and sex life?

10 p.m. Get into bed and log on to the dating apps. I change my age range from 28-45. I edit my profile to say I’m open to new adventures. I haven’t been on these for a while. Let’s see what happens when I shake the trees.


10 a.m. I’m extremely tired at work. I think I got four hours of sleep, and they were restless. I’m on my second cup of coffee.

11 a.m. Adam sends me a message about some book event tonight. Our vibe has shifted, and I think we both know it. I make a conscious decision to drink too much tonight and find out more about his personal life. I won’t do anything until I know all the variables.

2 p.m. In the meantime, I’ve matched with a million guys from last night. More than half of the matches are shady. I have to work … I can’t handle this level of correspondence today.

5 p.m. I live near the office, so I’m able to run home before this event with Adam. I pretend I have to let an electrician in to fix my AC (do electricians even handle AC problems?), because I don’t want Adam to know that I’m secretly just putting on a sluttier outfit and flossing my teeth.

7 p.m. The event is a pretentious, bookish thing, but the cocktails are amazing. Adam and I work the room together since our company is pretty well known and it’s normal to schmooze a bit. He looks great. He has scruff on his face that’s a bit gray and I’m surprised how much it turns me on. I keep looking at it.

He barely talks about his wife, so after drink No. 2, I say, “You never talk about your marriage.” He says, “Well, that’s probably because we’re separated.” I had no idea. He said that he’s afraid to talk about his personal life at work, especially in this era. Even now, he seems a bit paranoid. I said out loud, and several times, “You have my full consent to talk about your love life and sex life! In fact, I’m begging for it!” I almost put it in writing, but we both get a grip before that happens. Anyway, the wife is living out East. She allegedly cheated on him. He’s healing. It all seems a bit murky but maybe okay in terms of getting intimate at some point?

9 p.m. But it won’t be tonight. I go home to marinate on the new info.


10 a.m. Today I’m exhausted and hungover, but the good news is, I did the Bumble and Hinge deep dive last night and have a date set up for tonight. It’s a guy named Trevor who actually looks just like my ex. Same vibes (mysterious free spirits). Same jobs (writers).

Noon Texting with Trevor about where to meet up. He literally suggests the bar where I had my first date with my ex.

Here’s the deal with my ex. We were together for two years. We met when I was 25 and he was 30, at a book event much like last night’s. My ex was wonderful at first. It was a crazy year because he was doing a bunch of travel writing and brought me to the most beautiful places (it was still a WFH situation for me, so I could travel with my laptop and kinda have it all). We ate the greatest meals, rented Vespas in Europe, total fantasy material. Then we had to settle into reality back in New York. My ex had terrible mood swings when he was home and not chasing thrills around the world. He was drinking a lot, being shady about his whereabouts, and then he stopped wanting to have sex altogether with no explanation. I honestly don’t know what was really happening with him, but it made me feel ugly and unwanted and I had to get out. Two weeks after breaking up with him, I heard he had a new girlfriend and they were probably going to get married. Now I’ve blocked all our mutual friends and just try not to think about it. Of course, easier said than done.

4 p.m. Now that Adam and I have crossed that boundary, I go into his office to gossip a bit about last night and mention that I have a date tonight. I want to tease him a bit. He makes fun of our date spot because it’s “très Brooklyn,” and I can tell he’s jealous. Yay.

8 p.m. I walk into the très Brooklyn bar to meet Trevor. He’s late. He says his bike was giving him problems. He rode a bike to our date? I don’t know if that’s sexy or stupid. But he’s really cute. Puppy-dog cute and very flirtatious from the start. We order two dirty martinis.

He does not remind me of my ex in real life. He’s sweeter and a bit more grounded. He has nieces and nephews and talks about his family a lot. I’m not sure I’m attracted to him, though. He has very small hands, which throw me off. And then he asks to split the bill, which is a huge turnoff for me. You can call me an anti-feminist, but I want the guy to pay for the first-date drinks.

10 p.m. We hug at his bike, which is now just a gross detail to me. I get myself an Uber and text Adam that he was right, the whole date was cringe.

11 p.m. Adam writes back: I want details. Drinks tomorrow? 


9 a.m. I really need a mental-health day. My insomnia was bad last night, and the alcohol did not help. I get myself to work, but I definitely don’t feel good.

Noon I order a hangover meal for lunch. Ramen with a side of dumplings. I need the salt. The rest of the day is all about survival.

3 p.m. When I finally see Adam, I say to him, “Can we discuss the details of that thing tomorrow night instead?” There are some people around, so I’m trying to be coy. The act of having a secret between us — a secret potential affair brewing between us — is sexy and I like tempting fate by saying that out loud instead of via text. Adam says, “Copy.” And then he winks at me. More small-dick energy. Shit.

7 p.m. By the time I get home, I just want to cry. To make it worse, my roommates, who are a lesbian couple, are back from their summer in Maine. I love them, but I just want to be alone and weep and order a burrito with extra cheese.


8 a.m. Wake up feeling a little better. I slept maybe six hours. Not bad.

9 a.m. My roommates are up having coffee and I enjoy hearing about their summer. When they ask what I’ve been up to, I tell them I might have an affair with my boss. They tell me I totally should. But I think it’s because they like that  he’s older and owns an apartment and seems stable. A separated married guy with gray scruff and a slightly predatory vibe is still better than a tortured writer who was mean to me.

Noon My roommates sorta gave me permission to fuck Adam, I think. So I let him know I can hang out tonight if he can. He is a little bit vague about his plans, but I think it’s because he’s swamped at work.

4 p.m. He texts me the name of a dive bar in Brooklyn. I’m a little disappointed because I don’t even think there’s food there and it’s not what I was expecting. I was thinking a wine bar, a cheese plate, some dimly lit grown-up shit. Regardless, I give it a thumbs-up.

6 p.m. I go home first to shower, shave, and make myself look a lot better than I normally do at work.

8 p.m. Walk into the dive bar and it’s a cool scene. And there is food! Adam is already in a corner booth waiting for me, and I get the feeling that this is the booth where he brings a lot of women. We hug. We order drinks and some apps.

9 p.m. There is so much tension here. I’m attracted to him and he’s attracted to me, and the conversation is good, but I think we’re both scared. It feels like it’s on me to let him know that I want him and that whatever happens next is okay with me. Do I like Adam? I think so. I do worry that I don’t understand the nuances and intricacies of marriages and separations. But he says they don’t have kids and maybe it’s not that serious. He says it wasn’t an open marriage but she was unfaithful and now they’re heading toward divorce. It doesn’t seem so murky.  As I order myself another martini, I surrender to just having fun.

10 p.m. We are fully making out in this booth. It’s crazy good. He’s an amazing kisser. I’m drunk, so I whisper to him, “Do you know how much I want to fuck you? Take me home …” It doesn’t go over so great. He seems taken back by how forward I am. Maybe he’s more sober than I am.

11 p.m. I don’t remember the details, but I know it was Adam who said we shouldn’t go home together. He got cold feet, I think. I don’t know if it’s the work thing or the wife thing, but he gently and politely told me the night was over and we both had to go our own ways. Not only did he pay the bill but he got me an Uber.

Midnight. I’m lying in bed trying to process the night. I hope I didn’t fuck up my work situation. But maybe he likes me and this is the beginning of something. My head is spinning. I don’t know if I should be happy or scared about tonight, about all of it.


9 a.m. It’s the weekend. I’m hungover. I’ll have to wait until Monday to take the temperature on the Adam thing. Unless he texts me. I’m going to leave the ball in his court.

Noon My roommates and I go to Sunset Park to get some excellent Chinese food. They smoke a joint on the way, but I pass. I’m going to clean up my act this weekend and sober up.

3 p.m. I do some furniture shopping on Atlantic Avenue. I just need to make some changes. I consider looking for a new job. I consider moving to L.A. I remind myself I’m only 28 and everything will be okay.

8 p.m. My roomates and I watch Painkiller on Netflix. We binge the entire series in one night. It’s so dark. Taylor Kitsch is so fucking hot. Even as an opioid addict. The lesbians fully cosign.


9 a.m. I wake up feeling really disgusted by the fact that Adam didn’t text me yesterday. I don’t expect him to coddle me, but we had a rather intense night out, we work together, and it doesn’t seem like an appropriate “ghosting” situation.

10 a.m. I decide I don’t like Adam as a person and I should probably start looking for another job.

6 p.m. Still nothing from Adam. I decide to go to work tomorrow, holding my head up high and laughing the night off. If he mentions it, I’ll just say, “Oh, I was so drunk; that was so stupid. Anyway … back to work!” That’s my plan.

9 p.m. Instead of looking at the dating apps, I spend the rest of the night looking for new jobs.

10 p.m. It occurs to me that I haven’t thought about my ex in days. It’s something to be proud of.

The Sex Diaries column, which began in 2007, is the basis of a new docuseries on HBO.

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The Social Media Manager Who Makes a Move on Her Boss