The Lawyer Who Called Off Her Wedding

Photo-Illustration: Marylu Herrera

In this week’s story, a woman wonders if the co-worker she was having an affair with still wants to see her: 27, single, New York.

DAY ONE

8:30 a.m. Two weeks ago today I called off my engagement. Rob was my college boyfriend whom I loved but never lusted for. He was “husband material,” and I tried really hard to power through and marry him but I knew I wouldn’t be happy as his wife. The relationship was too dull for me. He was too dull for me. Plus, no one else knows this, but I was cheating on him in the end. It was with a guy named Theo who I work with at a law firm. It started a few months before I officially called things off. I’m still seeing him, but it’s gotten … weird.

10:50 a.m. I sneak downstairs to meet my mom for a quick hello. She’s walking by my office on the way to a doctor’s appointment. My entire family lives on the Upper West Side and my office is in Midtown West. She’s been great about the failed engagement. I tell her I feel ashamed and embarrassed. She says I should feel free.

1:30 p.m. A law-school friend, Emy, texts to see if I want to meet her at happy hour after work tomorrow. I say yes and feel a pang of anxiety. Everything feels like a foreign language right now. It’s the first time in my adult life I’m single. I’m not totally alone; I have my goldendoodle, Sylvia. My ex and I are currently sharing custody of her, which is not fun.

5 p.m. If one more person tells me to join a running group, I’m going to scream. I can’t think of anything worse.

7:30 p.m. On my way out the door, standing at the elevators, I remember that Theo comes back tomorrow after a long weekend away. We work at the same law firm but in different departments. We met in December at a holiday party. It’s so obvious and cliché what’s happened with us … when I was engaged, he wanted me desperately; now that I’m available, he’s pulling back. I didn’t leave Rob to be with Theo, but I definitely thought he’d be my next boyfriend or at least that things would rev up between us. But no, the minute I told him I ended things, Theo got weird. You’re probably thinking, No shit!

10 p.m. Sylvia sleeps with me and we like to curl up and watch TV together before bed. It’s my apartment, technically, so it was Rob who moved out. He gets Sylvia tomorrow. I can’t imagine doing this with children, it’s excruciating enough with a dog.

DAY TWO

7 a.m. I ran three miles this morning at the gym below my office.

9:30 a.m. No one at work knows about me and Theo, but they all know I called off an engagement to my boyfriend of ten years. They’re tiptoeing around me, which I’m honestly thankful for. I’m pretending I’m not scared, but I am. Nervous about what’s next, excited to finally find out who I really am …

1:45 p.m. My work bestie, Claudia, comes over to my desk and says she wants to set me up with her brother, Tony. I met him once at Claudia’s birthday drinks. He was hilarious — cracking jokes the whole night. Maybe too hilarious though. His personality is going to be too big for me right now. I tell her we’ll revisit “the Tony of it all” after the summer.

3 p.m. Rob texts that he’s picked up Sylvia. He still has the keys to my apartment. I see no reason to change them. He’s not a psychopath. Our texts are purely transactional. I want to say, “Are you okay?” But he doesn’t want to hear that from me. Of course he’s not okay. Our wedding was still a few months away, but it was a destination wedding, so a lot of people had bought tickets already. I couldn’t let the guilt of that stop me from living my truth, but it weighs heavily on me, what a mess I made for everyone.

5 p.m. First interaction with Theo today, in our coffee and snack room. We make small talk because other people are around. I’m insanely horny every time I see him. He’s hot in every way my ex was not: He’s dirty, he’s sexual, he’s confident. Our secret, of course, makes things steamier. Lately he’s texting me back less, saying things like, “We’re just casual, right?” I should play hard to get but I’m so fucking vulnerable right now.

7 p.m. Happy hour with Emy. The bar is dead since it’s a Tuesday and I end up venting about my life, which depresses us both. Emy’s been through something similar so it’s good to be with someone who understands. We don’t find any guys to flirt with so we call it after two drinks each. She walks me home since it’s on the way to her apartment. I tell her I don’t have a clear plan yet. It’s hard to explain my story to her without mentioning Theo but I swore on my life to him I’d never tell anyone we were having an affair.

10 p.m. No Sylvia. Not a peep from Theo — I haven’t reached out since last weekend when he made, then broke, plans with me to have dinner together (as in our first real, out-in-the-open date). But I definitely touch myself thinking about him. It’s impossible for me not to come the minute he enters me. When I’m with him, I have to distract myself completely from the sex so that I last more than five seconds. I never come more than once, so I need to savor that orgasm. My ex, Rob, was bad in bed. He was shy and tender and never fully a man about it.

DAY THREE

7 a.m. It’s nice to wake up feeling normalish. For the last two weeks, I feel like I woke up with bloodshot eyes from crying or from barely sleeping at all. My mom and sisters assure me it will get better each day.

9:30 a.m. Sipping coffee at my desk. Theo texts. “Want to hang out tonight?” I’m wet just from reading that. I guess ignoring him for a few days paid off. I don’t respond, intentionally.

12:50 a.m. Trying to focus on work but my mind keeps circling back to everything I lost with the Rob breakup: the friends who hate me for hurting him … the idea of being a young mom — which is something I always wanted, despite not wanting him.

6:30 p.m. Nice walk home from work. Alone, with music in my ears. I’m trying not to overthink the Theo thing tonight, but I still haven’t given him an answer, nor has he checked in again. I’ll get home, have something to eat with a glass of wine, and see how I feel.

8 p.m. I’m so horny! Finally I text Theo that I can be there by 9 p.m., if he’s good with that. I get a thumbs-up emoji. So I shower, get myself ready, and call an Uber.

9:30 p.m. Oh my God, the sex is so good. As always, I barely last a full minute once the penetration starts, but I think it’s hot (to him) the way I come so hard and so fast. We don’t talk about anything regarding my breakup or dating each other. We fuck, go downstairs and get some ice cream, sit on his stoop, and I call a car. It’s as simple as that. He’s not an asshole, but he’s definitely withholding. When I was engaged, he was as open and intimate as you can imagine. Now it’s like I can hear him thinking, Don’t give her any hope.

DAY FOUR

6:45 a.m. Wake up early again feeling anxious. Rob is bringing Sylvia to my place before he goes to work — he’s a lawyer too, but he works for his family so his hours are looser.

I leave for my office as early as possible so Rob and I don’t cross paths. He doesn’t want to see me — he made that clear the day I left him.

12:30 p.m. I have lunch with Claudia, my work friend, and decide that I’m going to tell her about Theo. It’s not healthy to bottle all this up. I am so mentally unbalanced right now that some honesty and transparency will do me good. She’s shocked when I tell her. Almost scandalized by it. She makes me feel a bit slutty and a bit freaky, and I immediately regret opening my mouth. I do think I can trust her, however.

3:30 p.m. My mom texts to remind me about a few loose ends. My parents and sisters took care of most of the wedding undoing, but a few things are still on my to-do list. One is canceling the hotel we were going to sleep at on our wedding night. It’s a really nice hotel near the place our wedding was supposed to be. I thought Rob and I would want to escape there for the night so I booked it. I have no idea why cancelling this room makes me so emotional, but as I call the reception desk, I cry while talking. It’s not like it’s a big deal, there’s no cancellation fee or anything, but it makes me weep.

5 p.m. For the first time since working at this firm (I started here as an intern in law school), I leave early. I don’t want to be seen crying at work. I fake a dental emergency and go home to sob into my pillow. What have I done?

8 p.m. Lying with Sylvia on the couch, ordering an entire chocolate cake off Uber Eats. I’m just going for it. Don’t look at my phone or anything for the rest of the night.

DAY FIVE

7:15 a.m. Wake up feeling sick of myself. Today is going to be a good day. I’m manifesting it!

9 a.m. It helps that I have a grueling work day ahead. I won’t be able to look up from my computer until nighttime. It’s a great distraction, as soul-crushing as this level of paperwork can be.

1:15 p.m. I get lunch and an iced latte because I need fuel. In line at the café, there are three guys in suits talking about some work trip. One is really hot. We make eye contact. I’m telling myself, “Go for it, introduce yourself.” But I don’t know how to break into their conversation. I feel like he’s having the same inner dialogue with himself. I try to smile flirtatiously and hope he’ll say something but then it’s time for me to order so I snap back into focus. He ends up grabbing his food when it’s ready and leaving. Maybe we’ll meet up here again some day.

2 p.m. As I eat at my desk, it occurs to me that those hopeful feelings at the café were a small victory.

4 p.m. Text my dog walker that it’s going to be a late one so I ask her to walk Sylvia one extra time this evening.

7 p.m. It’s a Friday night and I still have a few hours to put in so I step out for fresh air and decide a glass of wine won’t hurt me. There’s a hotel bar around the corner that’s supposed to be good, so I head that way. It’s kind of a miracle but there’s a group of businessmen at the bar having drinks together. They all come over to talk to me, since they’re all a bit drunk and ready to start the weekend. One of them is hot. His name is Colin. He has an Irish accent and says he’s lived here for the last few years. I fucking love the accent. I give him my number, swallow my last drop of wine, and go back to the office. Okay, Colin. This could be fun!

11 p.m. Home, finally. Sylvia makes me feel loved and missed. Just as I brush my teeth and wash my face, Colin texts, “You still out?” I guess he was too drunk to remember that I was technically still working when we met. I ignore it. I’d rather text with him when he’s sober tomorrow.

DAY SIX

8 a.m. Trying to make it to a gym class so I skip coffee and grab a power bar and go.

1 p.m. I try to make myself feel better by redecorating my apartment. The couch reminds me of Rob; the plates remind me of Rob.

2 p.m. I decide to go furniture shopping, which turns into clothes shopping, which turns into sexy new bra shopping. Meanwhile, I have not heard anything from Theo. I am starting to accept the fact that whatever we had was over. I’m not going to be a drama queen about it, as much as it stings.

6 p.m. Tonight I have a mixology class with my sister. It’s a gift she got me to cheer me up last week. I decide to go all out with my makeup and hair. Maybe the mixologist will be hot.

8 p.m. Okay, he’s not hot, he’s a cheeseball. But we have fun as sisters. She’s married and very stable, trying to have a baby, so we can only have so much fun, but it’s a great night out.

8:30 p.m. She gets on the subway to go home, and I text Colin and see if he wants to meet up and have a wild night out. I’m in the mood for that — the cocktails have me buzzing. I respond to his text from last night, “I’m out now … you?” After some back and forth, we decide that we’ll try to connect later in the night. He was at a dinner with friends in town from London. I decide to walk home and see where the night takes me on the way.

9 p.m. It took me to another bar in Soho! It looked like a good scene so I meandered in. I get a drink. I start talking to people and flirting. But I’m drunk now, and luckily I know better than to keep going or start hanging out with strangers, so I leave shortly after.

10 p.m. By the time I walk home, I’m slightly more sober, very sweaty, and not sure I can hang out with Colin. But that’s exactly when he texts. I give him my address and quickly shower and brush my teeth. I open the one bottle of wine I have in my apartment. It’s something expensive that was gifted to us at our engagement party. I try not to think about it.

11 p.m. Colin arrives. He’s quite sweaty too. He sheepishly asks if he can take a shower. It’s weird, but it’s hot out there, so I say it’s okay. He showers, comes out in a towel, and we start to kiss immediately. I’m happy he has condoms because he is a literal stranger. We end up fucking doggy style in my room. It’s good, not great, and I don’t come. The minute he’s done, I feel very used, even though I made this happen. I try to hide it, but I’m disgusted with myself and want him to leave. He kisses me on the cheek on the way out.

DAY SEVEN

9 a.m. Hungover, I decide I need therapy. One of my sisters is a psychologist, so I text her for recommendations and she quickly sends me a few names, and then she tells me how much she loves me, and supports me, and blah, blah, blah. I’m lucky to have my family.

3 p.m. I do some grocery shopping and get lots of healthy food. This will be the week I take good care of myself, I promise myself. This will be the week I give myself grace.

6 p.m. Most Sunday nights, my entire family gets together at one of our apartments. It’s a ritual we’ve had since we all grew up and left the nest. I know I need to be with loved ones, but I’m also really not up for it. I text the family chat that I’m having a “me day” and not going to make it, and everyone sends me their love without any pushback.

9 p.m. It’s a very quiet night at home. I cook dinner. I watch the movie Past Lives, which somehow I never saw. It warms my heart and makes me cry buckets of tears, but not in a depressing way. And then I go to sleep, feeling nearly whole.

Want to submit a sex diary? Email sexdiaries@nymag.com and tell us a little about yourself (and read our submission terms here.)