sex diaries

The Graphic Designer Waking Up Next to Her Ex’s Best Friend

Illustration: by Marylu E. Herrera

This week, a woman fresh off a breakup wonders if maybe she wants a relationship after all: 24, single, Brooklyn.


8 a.m. I woke up pretty astonished by myself. I’m in bed with Jonah, my ex-boyfriend’s best friend. I barely remember what happened last night. I remember, but it’s blurry.

9 a.m. We’re having coffee. The one hot thing is how wrong all of this is. I like Jonah more knowing he’s evil enough to sleep with his best friend’s ex-girlfriend only two weeks after we broke up. But I’m also sickened to think I hooked up with such a dick. As for me, oh yes, I’m a garbage person too.

10 a.m. “I’m sorry that it wasn’t more memorable, but we didn’t fuck last night, right?” I say bluntly to Jonah. We both laugh a little and then talk about how drunk we were. He confirms that we didn’t, we just came close. I only kind of forget the very last part of the night, which is when we both passed out in his bed after hooking up.

3 p.m. After another nap at Jonah’s and some lunch — no hooking up — I put on my earphones and head home. He’s in Manhattan and I’m in Brooklyn, so I enjoy walking the bridge despite my hangover.

5 p.m. I don’t tell my roommates or my friends about last night. No one even knows we met up. It’s nice having a secret.

8 p.m. Early bedtime. I’m wiped out. I giggle to myself thinking that the only reason I went out with Jonah was because he works in the wine business and I wanted some free, good wine and had never tasted any that wasn’t the cheapest on the menu. Of course, it wasn’t quite that innocent. When I texted him asking to come over to his place to test out his collection, I knew what might happen.

And the wine was indeed amazing. How will I ever go back to my shitty stuff? Oh well, that’s probably the least of my problems at the moment.


9 a.m. Slept like a baby until I had a weird dream in the early hours of the morning that Jonah tricked me into going into an extension of his apartment that was really, like, a kill room. He was going to kill me, all Dexter style. I woke up in a sweat.

Noon: I tell my friend Pia I need to do groceries, so she tags along to Whole Foods. Afterward we get a piece of pie and coffee nearby. I love Pia because she’s very funny and seems to get me, in all my twisted ways.

I say twisted because I used to cheat on my boyfriend and it was all pretty fucked-up for a while. We met our last year in college and were together for four years. He was always good to me. It was just too boring and the sex never did it for me, and I’m a very horny person. About a year into our relationship, I slept with someone else, and it just spiraled from there. I always thought I had to get some stuff out of my system to be a good girlfriend to him; that I was kind of doing a good thing for our relationship. Obviously I was crazy to tell myself that. In the end, he never caught me cheating. But I broke up with him because it just got too out of hand. I was lying all the time, flirting with his friends behind his back, even though I never crossed the line with any of them. Jonah and I had a vibe, and I think we both saw the devil in each other’s eyes, but waiting until the breakup was an unspoken “ethical”-ish choice.

3 p.m. Speaking of Jonah, he wants to see me again tonight. I’m not sure. I wasn’t so impressed by our physical chemistry. I play hard to get and tell him I’m busy. Not sure if it’s worth the drama with that one — my ex will definitely find out and he has been hurt enough.

7 p.m. I’m swiping online to see if someone wants to have a very easy, very local drink. I’m not up for much else.

10 p.m. Chatting with a guy named Bobby who seems cool, but I’ll resume our convo tomorrow.


8 a.m. The workweek begins! I work at a store in the city where mostly everyone else is queer and I’m definitely the youngest and straightest. But it’s a blast. Everyone has hilarious stories come Monday morning. I handle graphic design.

10 a.m. Bobby is texting me and asking about tonight. I know I’m getting my period later in the week, so if I want to fool around, tonight is my safest bet. He looks like my type: tall, dark, and strong. Jonah is so puny. Out of the blue, I kind of want to throw up thinking about waking up in his bed.

12:30 p.m. There is a restaurant near my store, so I tell Bobby we can meet for a drink after work.

6 p.m. Get a quick blow-out — they serve champagne there. So I’m off to a good start.

7 p.m. Bobby walks into the restaurant; I’m sitting at the bar. Of course he’s not quite as hot as in the photos, but he’s got a cool vibe and he’s definitely got a good body. He reminds me of a college baseball player.

8 p.m. So Bobby isn’t the sharpest knife in the drawer, but he’s sweet. He laughs a lot. He has a deep voice and, what can I say, I’m very curious about his cock. More drinks, please!

10:30 p.m. I’m ready for the “your place or mine?” conversation, but he says he actually has to go home. He has some Zoom call with Europe at 6:30 a.m. and he’s all worked up about being in bad shape for it. He hugs me goodbye as we both walk to different subways.

11 p.m. I feel rejected but … what can ya do?


10:15 a.m. Ugh, I’m hungover. For nothing!

12:30 p.m. I try one of those hot yoga classes because I heard they cure hangovers, and I just want to vomit the entire time.

3 p.m. I don’t know. When I’m hungover and feeling rejected, it makes me miss my ex. I know I’m not destined for a serious relationship right now, or maybe ever, so once I figured that out about myself, I ended things. It’s just that right now I kind of hate myself for it.

6 p.m. I text Bobby to see how his Zoom went and because I’m on the subway home and feeling bored, and, like, I have nothing to lose.

10 p.m. Still no response. I’ve been dismissed. It’s okay.

11 p.m. Lay in bed wondering if I had bad breath or something.


11 a.m. Work meetings are actually fun for me. I love to drink in the place, just look at everyone one by one, how unique and complex we all are. It’s a super-diverse company and everyone has a really big and interesting personality. I’m lucky to love where I work.

2 p.m. My friend who is my third roommate (the three of us went to college together) texts that we have to rethink the rent situation. We rent our place from her family, so it’s cheap. But I wonder if that’s about to change. I start to feel a little bit sick. If she ups our rent, I might have to move home with my parents in New Jersey. The only reason I can live on my own is because of this rent situation. She asks if we can all meet up tonight to talk. I’m scared shitless.

6 p.m. I pick up a bottle of wine on the way home. I wish I could remember what Jonah said I liked and didn’t like from our debaucherous wine night. I text him to remind me and he writes back, “Shit, no clue.” He’s blowing me off. I get it. He felt anxious about my ex finding out and probably had a come-to-Jesus moment. We’re better off not really talking.

9 p.m. Neither of the roommates is home yet, as both are stuck at their own work things, so we decide to address everything tomorrow night instead. I have a terrible feeling about all of it.

10 p.m. Two glasses of wine later, I’m online dating and trying to find some guys I can engage with. It’s rough out there!


7:30 a.m. I see the roommate whose parents own the apartment while we’re both rushing to get out. I’m just like, “So are we getting kicked out?” I don’t want her to know that I was up all night worrying about it. I try to sound super-casual. She’s like, “No, no! But my parents want to adjust what we each pay. Like, they don’t think it’s fair that everyone is getting a free ride. Ya know?” She seems nervous and says she has to rush but we’ll discuss tonight. Seems a little avoidant to me, but at least I know what’s coming.

11 a.m. I look around online at other rentals and various options, and I’m just not sure what I’m going to do.

3 p.m. Just for fun, I look at rentals in cities like Buenos Aires, Paris, and Amsterdam. London, I already know, will be too expensive. I look at L.A., then Austin, then Miami. Where do I belong?

8 p.m. Okay so we’re all at home and the roommate with all the power says her parents want to charge us “market rate” for the rental, but they’re not making her pay anything because she’s transitioning careers. Basically it’s going to be unattainable for me. There’s no way. We have a few days to give them an answer, and a month to move out if we can’t swing it.

9 p.m. I can’t be mad about it, but I end up going into my room and having a minor anxiety attack. It’s times like this that I really miss my boyfriend. He would have helped me figure it out. I’m on my own now. Also this feels like karma.


8:30 a.m. Before work, I call my parents to fill them in on everything. I love them, but they’re going to want me to come home, and that’s the last thing I want to do. Just as predicted, my mom is practically getting my bedroom ready for me before we hang up. At least someone loves me … but no, I don’t want to move home. That’s a last resort.

11:30 p.m. So my ex is actually in real estate. I text and ask if he has ten minutes to talk. “Not about anything serious,” I say, knowing he won’t want to talk if it’s about our breakup. I really hurt him and he’s done with me romantically. He says, “Sure.” I take it further and suggest we meet for a walk in Central Park during our lunch breaks.

1 p.m. It’s good to see him and it’s also very hard. He’s closed off to me. I wonder if he knows about Jonah. He doesn’t have a lot of time, but he suggests a few rent-stabilized buildings that I might be able to get into. It’s not a romantic walk or anything like that. It’s pretty depressing, if I’m being honest.

6 p.m. I’ve blown off the entire day at work thinking about real estate and my living situation.

7 p.m. As I walk home, again over the Brooklyn Bridge, I feel like I want another boyfriend. I don’t know … it’s so hard being alone! I try to think about my life as a whole and what I can do to make some adjustments. I’m only 24, but maybe I’m ready to make some adult decisions. Maybe.

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The Graphic Designer Waking Up Next to Her Ex’s Best Friend