sex diaries

The Lawyer Having Breakup Sex Before Work

Photo-Illustration: Marylu Herrera

This week, a lawyer gets dumped by her boyfriend, but not before a few more hot hookups: 30, single, New York.


9:12 a.m. I am awake. I was out until 3 last night, but at least I got about five hours of sleep.

10 a.m. My roommate left coffee in the pot, so I pour a cup and heat it in the microwave. Microwaved coffee is tragic, but I’m a bit hungover and regretting fighting with my boyfriend last night. We met on Bumble and have been together for two years.

We were at a club for his friend’s birthday, and I drank too much and started yelling at him about not proposing to me yet and not moving our relationship along fast enough. I said some mean things in regards to his family (parents are divorced, siblings are all at war) and how he has a fucked-up relationship with love. I think I went below the belt …

1 p.m. I’m sweating out the alcohol at the gym.

3 p.m. Finally, I text him. “We okay, babe?”

5 p.m. I’m being lazy on the couch, thinking about what to order in for dinner. He hasn’t texted me back and I feel anxious.

6 p.m. I call him. He doesn’t pick up.

9 p.m. He’s not going to communicate with me today. I just know it. I make myself get into bed and my body naturally falls asleep. I desperately need a good night of rest.


8 a.m. Now I’m really worried about things with my boyfriend. One messy night can’t just end things? Did we have cracks in our foundation? Sure. I think we have different definitions of what our 30s should look like. I’d like to settle down — I want to be a mom and a wife and a successful working woman. He wants to quit his job and travel and experiment with sex and drugs. We are both lawyers who don’t like our jobs.

But there was a lot of good between us … We have amazing sexual chemistry. I love fucking him. I want sex with him all the time. I like his politics. We love the same music, food, and movies. We’re compatible. I just don’t want it all to go away because of one big fight!

1 p.m. I take a Pilates class with my best friend. She’s more pissed off than I am that my boyfriend is still ignoring me. She thinks it’s a huge red flag and can’t understand why I don’t. The truth is, I don’t have that much experience with relationships, so I don’t know what’s “normal.” My last serious boyfriend was in college and we were so young. I leave the workout feeling more upset than I already was.

2 p.m. I call my boyfriend again. No answer. I can’t remember exactly what I said at the club but could it have been that bad?

5 p.m. Finally, a text from him. It’s long. He’s breaking up with me. It basically says that we want different things, and that I don’t deserve to be strung along by him, and the fight really opened his eyes to the kind of pain I was in from being with someone who is “a bit lost” like him. I’m shocked. He is dumping me. 

8 p.m. Spend the night crying. My roommate listens and hugs me all night. She even makes me homemade chicken soup.

10 p.m. I write him back a text that basically begs for one more chance. I want to fight for us. It can’t just end like this?

11:50 p.m. No response and I have a big day at work tomorrow, so I go to sleep. My heart hurts. Nothing about this feels right.


8 a.m. On my way into the office in midtown trying to think only about work. My parents sacrificed so much for me to go to law school, and I’m not going to be the hot mess who lets boy problems get in the way of work.

Noon Have not looked up from my desk all day. Ignoring my phone.

2 p.m. Check my phone to see a text from him. He asks if I want to have a drink tomorrow. He says we can talk about things. It’s not a very loving text, so I take this as a bad sign, but at least it’s something.

5 p.m. I am only now eating lunch. I feel numb.

9 p.m. I leave work and decide to walk home, from midtown to the Lower East Side. The cold air stings my face and it’s invigorating. I think about what I want to say tomorrow. I am not going to pretend that I don’t want to get married and have kids. I have to be myself, but maybe there’s a middle ground. Maybe I’ve been too rigid. Maybe I’m anal or conservative or uncool. My mind is playing tricks on me. How do I win him back without changing my truth?

11 p.m. In bed. I finger myself thinking of him. I think about his gorgeous dick in my mouth; his fingers in my ass as I come; his teeth on my nipples. Maybe tomorrow we just fuck all night and erase everything from the past week? Maybe that’s the healthiest move.


9 a.m. Work is a grind today. My goal is to sneak out and get a mani-pedi and a wax at some point. For some reason I’m really horny.

1 p.m. I sneak away for a mani-pedi-wax. I text him about where to meet up, and he picks a place right near his apartment, which is in midtown near my office.

5 p.m. Find out my colleague is pregnant. I’m happy for her but am reminded that I really want to be a mom. I have a plan for myself, and everything with my boyfriend messes that up.

7:30 p.m. I go right from the office to meet my boyfriend. He’s already there having a beer. We hug for at least one full minute.

We sit across from each other and I take his hands. “I don’t want to break up,” I say. He doesn’t really answer me back. Now I’m crying. “Please, let’s keep trying. Let’s keep us alive.” He just kind of stares at me. He isn’t being mean or anything, but he’s not responding the way I want him to. It’s as if he’s already turned the page. How could he do that so quickly?

8:30 p.m. We’re both on our third drink and the conversation is going nowhere, so I suggest we have good-bye sex. There’s definitely a part of me that thinks if the sex is hot enough, he’ll take me back. But also, I’m just dying for it at this point.

9:30 p.m. We’re barely inside his apartment before we’re fucking. Our coats are still on and he’s inside me. I come almost instantly, and he comes shortly after. But literally, my coat is still on, and I don’t know if I’m supposed to pull up my jeans and just go home or if I’m allowed to stay for a while. I am still in shock that any of this is happening.

10 p.m. He says, “You should go.” So I leave. And I just cry and cry and cry the whole way home.


7 a.m. Realize I left my wallet at his house. It truly was not intentional. I took it out of my coat when we were fucking because I was afraid it was going to fall out. I can get by using my phone and Apple Pay, but I text him and ask to stop by his apartment before work to get it. He doesn’t live that far from my office. He says: “Okay.”

8 a.m. He’s dressed for work and smells so sexy. I grab my wallet and say, “Fuck me one last time.” Then I bend over his kitchen table and he fucks me in a way that feels almost obligatory. It’s as if he’s fucking me to make me go away, once and for all. I come, but the moment feels dark. We hug and go our own ways to our offices. It’s awkward.

3 p.m. My day sucks. I’m in a horrible mood. I can’t believe I’m single again.

7 p.m. I call my friends and family while I walk home from work and tell them that the relationship is over. Everyone says it’s for the best. Maybe one day I’ll agree with them, but it’s too soon right now.

9 p.m. I’m doing laundry and cleaning my apartment hoping to get a text from him that he’s changed his mind.

11 p.m. No texts. It’s so fucking weird to think that I’ll never see or speak to this man again.


8 a.m. I slept like shit. Was this all a dream?

10 a.m. I tell a few colleagues that I’m back on the market again. Everyone wants to fix me up. I tell them I’m not ready. There’s not one bone in my body that wants to meet someone else right now. Also, who will ever satisfy me sexually like he did? It was too good to be true, I guess.

4 p.m. My boss tells me we have a work trip coming up and that we’re all going to Los Angeles for a week. I’m from L.A. and this should make me very excited, but I feel lifeless and unemotional. I’m like a zombie. I just want to keep grinding at work and not think about life or feelings or anything besides my path to success.

9 p.m. I take a sleeping pill from my roommate to knock myself out and make the day end.


7 a.m. Wake up feeling slightly better. Maybe it will only take a few days to recover, but every time I blink, I imagine having sex with him. I can’t get the images out of my head.

10 a.m. I’m in a better mood at work today. We have a work dinner tonight at a restaurant I’ve heard a lot about, and I’m excited to eat a great meal and feel less tense.

2 p.m. Every minute of the day is a struggle to not text my ex-boyfriend, but today I go about 20 minutes without thinking of him. That’s a start.

9 p.m. There’s about ten of us at a round table at this trendy restaurant. I’m feeling a little better. For the first time in days, I look around the room and think, “Hmm … maybe there’s someone special here for me?”

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

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The Lawyer Having Breakup Sex Before Work