sex diaries

This Week’s Sex Diary: The Woman Who’s Worried Her Co-worker Is Dating Her Ex

Photo-Illustration: Marylu Herrera

In this week’s story, an office manager gets ghosted and stood up and has to block some numbers as she tries to put herself back out there: 29, single, New York. 


8 a.m. A quick shower to start the day. My job is bumming me out lately, so I try to sing while I’m in there. I go with “All I Want for Christmas Is You,” by Mariah Carey.

11 a.m. Said job — office manager for an advertising agency — is busy. It’s always as if I’m the personal assistant for 40 people (the whole office). I will say, I’m very good at it. And that’s a source of pride. I’m finally putting myself out there to date, after a breakup that ended three months ago, and being good at my work is good for my confidence.

3 p.m. Tony texts to confirm our drinks date tonight, then asks if I have a place in mind. Kind of a turnoff. I like when they pick … it feels more romantic. I met him online. He seems nice and funny, although I’m definitely going to be several inches taller than him. I’m almost six feet, so I’m taller than most guys. I try not to be too fussy about it. After all, I need someone to accept my height too. So, in the spirit of height inclusivity, I’m meeting up with a five-foot-eight man, who — doing Tinder math here — is probably actually five-foot-six.

But I’m not going to tell him where. My head is filled with enough busywork. “You pick,” I write.

4 p.m. He suggests Chipotle. I’m not kidding. I can’t believe my eyes. Several minutes later, he writes back, “LOL. JUST KIDDING. How about …” and then suggests a bar attached to a cool hotel in downtown New York. I’m cracking up. Nice one, Tony.

5 p.m. Leave work to go home and shower again. I like to smell fresh just in case things get exciting later.

7:30 p.m. Waiting for Tony at the bar he suggested.

8 p.m. Still waiting. I text to see if he’s okay. He writes back, “Full disclosure, I had another date before ours and it’s actually going well, so I have to reschedule.” For the second time today, I am shocked to my core. I don’t write back. I put on coat, pay the bill for my barely sipped glass of wine, and leave.


7 a.m. I have washed my face and brushed my teeth three times each, and I still feel disgusting from last night. That was just such a gross experience. Fuck that dude!

10 a.m. It’s always embarrassing telling people at work when my dates are flops. This wasn’t even real enough to be a flop! But I tell everyone who keeps up with my love life and they join me in the nausea over this man, and we all move on.

1 p.m. Someone I work with recently told me she saw my ex, Anton, on a dating app. She made it sound like she totally ignored him, but when I see her around the office today, I get a strange intuition that maybe she’s met up with him. I can actually see them together. He’s a tall, super-handsome guy who used to be a college basketball player and is now in finance. And she’s, I don’t know how to put it … a Kardashian clone of some sort. Visually, they’d look right together. After five years together, my ex and I broke up a few months ago because he couldn’t give me the love or affection I needed. He never planned anything for my birthday. He never asked about my work or my family, and put in zero effort with my friends. I was always like, “He’s so good to me behind closed doors.” But that got old. He made me feel like a pain-in-the-ass girlfriend, when I think my relationship standards were actually pretty normal. It’s been hard to move on, but my friends and family have been amazing and I know I’ll be okay.

6 p.m. After work, I get my eyebrows waxed and manicure touched up. I’ve found that the more I put into my external appearance, the sexier and more motivated I feel about putting myself out there again.

9 p.m. I watch that documentary about the Twin Flames cult and mindlessly swipe through the apps. I’m lonely, but I have a lot of hope that I’ll meet my next man soon.


8 a.m. I get dressed knowing I have to go from work to a company party to a singles event. I decide on a pantsuit with a corset underneath.

11:30 a.m. It’s not a good day to fight a migraine. I get horrible ones that often make me throw up. I take two Motrin since I don’t have anything strong and try to wait it out.

5:30 p.m. I feel better just in time for the holiday party. But I’m not going to drink. One of my co-workers continues to tell me that alcohol cures headaches, but I’m just not buying it. This same person takes a shot the minute we get to this bar that my company has rented out (and that I organized and planned). This same person starts flirting with me as the night goes on. And this same person is married. He doesn’t do anything obviously unprofessional, like touch me or anything, but he’s getting a bit too close and asking me weird stuff about being single in my 20s. I find another group to hang with.

9 p.m. It’s a Christmas miracle, but the singles party I’m going to is practically down the street. I make my way in that direction. I’m meeting two girlfriends there. We bought tickets but don’t know what to expect. It’s like a singles-only mingling mixer-type thing.

9:30 p.m. Okay, I don’t want to sound mean, but every man here is the size of a small child. How am I supposed to work with this?

10:30 p.m. I am shocked that I remain the tallest person in the room. But as I head out the door, a man who is about my height enters the party. I say something like, “You can take over for the tall people; I’m going home.” He laughs and then says, “Wait, give me your number first!” I give it to him and then I call an Uber. It’s freezing cold, but I’m smiling while shivering. That was a cute interaction! I didn’t even get his name, though.


10 a.m. My whole office is hung-over. It feels great to be the functional, bright-eyed one.

1 p.m. I’m thrilled when I get a text that says, “Tall Stranger Here … Would you be interested in a tall glass of Champagne — or insert drink of your choice — with me sometime?” What a great text, right?! Is it weird he hasn’t revealed his name yet? Seems deliberate at this point.

2 p.m. I write back with a heart emoji and then ask for his name. He says, “Why? So you can Google me?” Dude is making me beg for his fucking name? This is weird. He has one more shot.

5 p.m. Text comes in. “I’m sorry. I’m a really private guy.” Jesus Christ. I’m not responding. In fact, I block him.

9 p.m. Back watching the Twin Flames doc. What is my life? I’m having such bad luck this week!


8 a.m. Twice a month, a few of us from work volunteer at a local food bank, which is at a warehouse in the Bronx. One of my colleagues has a car, so we all meet in the city and drive there.

1 p.m. Back at the office, it’s somewhat quiet. I try to converse with some of the guys I’ve matched with, but I’m feeling worn down by it all. Still, I make a plan with one of them for tomorrow night.

3 p.m. The girl who I think might be dating my ex-boyfriend was not at our holiday party and when I see her, I tell her she was missed. She says, “I know. I’m sorry. I had something else I couldn’t get out of.” This is where I get real shady and look at my ex’s Instagram. I see that on the same night of our holiday party, he had a birthday party. There is only one picture I can dig up of his birthday party, and I search for a sign of this girl. I don’t get what I look for, but man, my hunch is strong! Do I care? Not really. I mean, yeah, it stings, but I can’t tell if I’m just being delusional.

7 p.m. I schedule dates for tomorrow and the next night while finishing up Dancing With the Stars. Honestly, dating is like having a job, on top of a real job. It’s kind of the pits.


9 a.m. On Saturdays, I work out. I hit the gym for a few hours, then I do the sauna and steam. I listen to hip-hop and just zone out.

1 p.m. While I’m getting groceries for the week, my date for tonight asks if I want to go to a party with him. He’s being a bit cagey.

2 p.m. After some back-and-forth, he reveals that it’s a kink party. This guy seems cool at this point, and I’m interested in him, but really? For a first date? I tell him I’ll give him an out, and that he can go to the kink party, and we can reschedule. I’m really not comfortable with the idea of going to a sex party with a stranger. He responds only with a thumbs-up emoji … and then I ask when we should reschedule our date for. He does not respond.

5 p.m. So here I am preparing for yet another night alone.

8 p.m. My friend gave me a vibrator for my birthday. I take it out and give it a try. I don’t have a lot of experience with sex toys. I’ve always had a boyfriend and I’m just not a super-sexual person. I like sex when I really love someone, but it’s not on my brain otherwise. But the vibe feels good, and I orgasm. I put it in my nightstand and have a feeling it will not be collecting dust in there.


8 a.m. I wake up with a whole day ahead of me. Days like this make me wonder if I should be living closer to home, which is in the Midwest, so I could spend lazy days with my nieces and nephews or with my parents, who miss me. I made another app date for tonight; I guess I’ll fuck around and do nothing until then. And let’s be honest, will that date even happen?

10 a.m. The guy I’m meeting tonight, Rob, does seem like a decent person… no red flags so far. He’s in marketing and went to the same college as my best friend, and when I checked him out with her, she had a vague memory that he was “cute-ish, and not a serial killer or anything.” I mean, that’s the standard at this point, isn’t it?

2 p.m. Take out the vibrator. Why not!? I’ve never watched online porn — it’s all a mystery to me. Like, what website do I go to? So I just kind of go zen while I do it. Something about a clear mind makes the orgasm feel really good.

4 p.m. Rob texts that he somehow scored a reservation at a sushi restaurant that looks absolutely delicious. I love his initiative. This could actually be good!

5 p.m. I start to slowly get ready, shower and shave, and have a glass of white wine while picking out my outfit.

7 p.m. I arrive at the restaurant in a really pleasant mood. Rob arrives about a minute after me. We are both still all bundled up in our winter gear, so we give each other big, cushion-y hugs hello. He is taller than me! And actually here, in the flesh. And not a serial killer or at a sex party, and he has a real name that I openly Googled without any drama. We are off to a great start.

9 p.m. Dinner was lovely. The food was epic. We decide to grab a drink nearby. We like each other, I can tell!

10:30 p.m. After much flirting and drinking and cheer, we decide to call it a night and go our separate ways. As we get up to leave the bar table, Rob asks if he can kiss me before the date is over. And then he asks if we can do it again, sometime soon. I say, “I’d love that!” I can’t conceal the gigantic smile that’s bursting all over my face, but that’s okay, because that’s just who I am.

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The Woman Who’s Worried Her Co-worker Is Dating Her Ex