¡hola papi!

‘I Hooked Up With My Ex. Now What?’

Illustration: Pedro Nekoi

This column first ran in John Paul Brammer’s Hola Papi newsletter, which you can subscribe to on Substack.

¡Hola, Papi!

My ex and I have been really close. We’ve been the best of friends for the last two years. Recently, we reinitiated a sexual relationship. The issue is I don’t know where this is going. The last time he broke up with me, it really, really hurt. It was difficult to move on from. I felt like I had invested a lot into our relationship, and with the intensifying effects of the pandemic, it felt like I didn’t have any place to go from there. 

Now I’m confused. We had sex, and it was wonderful. It felt better than when we were together. But I don’t know if this is sustainable. I’m both afraid to try to move forward and I’m afraid that staying in this status quo will just lead to us hurting each other. Any advice? 

Back for Seconds

Hey there, BFS!

I don’t think you need a particularly wise advice columnist to tell you that sleeping with your ex is a bad idea, right? It’s in the handbook we all get on the first day of Advice-Columnist School for Exceptional Phonies. You just shouldn’t do it. Have I done it? Well, yes. But I do a lot of things in the name of research.

Take it from me, BFS. Something can feel good, even great in the moment, and still not be worth it in the long run. Pleasure is Pain’s most reliable wingman.

I’ll point out a few red flags. Grant you, I don’t have a lot to go on here, and, if you haven’t noticed, I am not you, so I’m unfamiliar with the finer points of your dynamic with this person. But you say you’re “confused” and “afraid.” You just had a spontaneous hookup with this person, yet you refer to the present situation as the “status quo.”

Confusion, fear, and feeling like you’re back at square one are not the building blocks of a fruitful partnership. Also of concern is that, as you said, you were the one who invested a lot into this relationship. When you say “we reinitiated a sexual relationship,” honestly ask yourself, Was it perfectly mutual, or was it more on his terms? Was this done out of convenience, loneliness, or familiarity on either of your parts? In other words, is this you once again being the more invested party?

These are important questions to ask if you want to maintain a friendship with this person, which, by the way, is totally possible! It’s also possible, take it from me, to have sex with friends or to have … let’s call them unconventional dynamics … with people who break the mold. Sure, sure. But such dalliances shouldn’t be tossing you into emotional turmoil.

My advice is to address your ex head-on. Express how you feel about the hookup, and ask about his feelings. Say that his friendship is important to you and that in order to maintain it, you need to get over your previous romantic relationship, which will be impossible if you’re having sex with each other right now.

If indeed this is reflective of what you want, then you’ll need to take some time and space apart. I use the wince test. If the idea of this person dating someone else or hooking up with other people makes me wince, if it feels like a little thorn in the heart, then I’m not ready for a platonic friendship with them.

I’m happily friends with some of the people I’ve dated, but it’s taken time. Each of those friendships has traveled a unique path with different requirements and timelines. Regardless, to the surprise of no one, I do not advise getting back together. Could it happen someday? I suppose I don’t know, but I don’t think it’s the move right now.

There are other guys out there you could be investing emotions into who carry fewer complications. Guys are, like, mad common. Guys everywhere. I see more guys on a daily basis than I see pigeons or rats or dogs, all things that are similar to guys in different ways when you think about it.

Think about it.

Con mucho amor,

Originally published on May 10, 2023.

This column first ran in John Paul Brammer’s Hola Papi newsletter, which you can subscribe to on Substack. Purchase JP Brammer’s book, Hola Papi: How to Come Out in a Walmart Parking Lot and Other Life Lessonshere.

‘I Hooked Up With My Ex. Now What?’