I'm sleeping with an ex who is moving in with her ex.

How badly am I fucking up? Should I cut my losses or really fight for this?

Here’s The Thing is an advice column/newsletter where I mostly beg people to either stop dating someone or to ask their crush out. Or I talk about weird things that came to my mind that no one is paying me to write about. I can never decide if I should capitalize the “the” in Here’s The Thing or not; apologies on lack of consistency. 


Last fall I matched with a girl on Hinge and we almost immediately hit it off. We live a few blocks from each other in Brooklyn but matched while I was at my parents’ house dealing with a family emergency. The day I drove back I parked the car and immediately texted her to get a drink. We met up and ended up sleeping together (bad in COVID times, I know) and it was hard to tell what would happen. Then a week later she came over and then we just kept seeing each other. We said the usual stuff you say when you first start dating someone (scary to say you like someone new, not looking for anything serious, etc) but it quickly started to become more than just sleeping together. 

She would sometimes drunkenly throw out lines like “I can’t date you, you’re five years younger than me!” Obviously that didn’t matter and we kept dating and it was good and it was fun. Fast forward to January and she tells me her ex is back in the picture and “going through it” so she feels like she doesn’t know what she wants now. Inevitably she chooses him and our breakup is definitely but drawn out. Lots of texts about all the feelings we still have for each other, lots of tears, but no changes. She was still with this guy (backstory is they used to live together then she moved out and they were on again/off again). 

Then a few weeks ago she came over and we started sleeping with each other again even though she’s still with this guy. And honestly? I’ve felt very little guilt over it despite generally being a good guy who has moral quandaries about a lot of shit. Anyway, after about 2 weeks of this little affair I just learned she moved in with the guy again. Doesn’t make me feel guilty about this still, but it’s seeming less and less like our future can happen, even though the afternoon this bombshell dropped she continued saying she loves me and all but admitting that she wants to be able to be with me. 

I guess my question is: do I keep doing this until it disintegrates completely or cut it off now before a real honest to god falling out? My thing is the past couple weeks of sleeping together again has felt way better than the two months of painfully admitting feelings and not acting on them. I just don’t know what to do. We’ve known each other 6 months and have this strong connection that is putting up a real fight against this other guy she’s known for at least 5 years. How badly am I fucking up? Should I cut my losses or really fight for this?

submit a question


I’m going to be super frank with you firstly because that’s kind of the point of this newsletter, but secondly because I think you need someone to be at this point. Either no one in your life has been frank with you about this situation and it will help you or everyone in your life has been frank with you about this situation and I can add my vote to theirs.

So, in the spirit of perhaps-a-notch-too-harsh-honesty: What the hell “future” are you talking about?

A future of continuing to fuck while she lives with her boyfriend? A future of what? Her moving out of the apartment they just moved into to live with you until she finds someone else that she wants even more? Or until you find someone else? Until this gets real and not “fun” for you two?

I do not think there is any way to “fight” for this because she already has and HAD the option to be with you exclusively and she chose not to. What could you possibly do to make her stop seeing both of you at the same time—eating her cake and having an apartment with it, too? I mean what are you going to do? Venmo her $7,000 if she “picks” you? What is the arrangement? That she move in with you and fuck him on the side instead? I mean! What!

You also mention that your connection is “fighting” against theirs and perhaps winning, but of course it is: you aren’t doing day-in-day-out relationship shit. You two are fucking clandestinely. OF COURSE that’s “winning” some imaginary battle of what’s more exciting. I know that you two have had a bunch of emotion-laden confessions of love and like, which might make it feel as if this relationship is More Than Just Fun Sex, but let me be clear: those declarations are not actual emotional hard work, they are indulgent outpourings that build drama (and thus excitement) right into the very foundation of your affair. Late night “I miss you”s are a pale imitation of the work that goes into a loving, functional relationship.

I think that her being in a relationship with someone else—a dreadfully dysfunctional relationship—is a large part of the thrill for you both. Of course you don’t feel guilty; you’re too busy being excited about this indiscretion! Perhaps there were similar reasons you both weren’t careful about COVID protocol: you’re both begging someone or something to excite you. And, by cheating on her “ex” (who is actually NOT her ex anymore; you are her ex now) with you, you have both manufactured excitement for one another.

To put this severely bluntly: I do not think there is any possible future in which you two maintain the level of fun you’re currently having longterm. In fact, I do not think that you two actually want an actual relationship together—the picking-out-a-couch, splitting-a-deposit-on-an-apartment, muddling-thorough-a-meet-the-parents-dinner, buying-diarrhea-medicine-for-one-another parts of a relationship. What you both profess to be love is, frankly, not it. Love requires an amount of showing up, an honesty, and a mutuality that this relationship cannot possibly ever reach; the relationship has been kneecapped by its own origin of infidelity.

I’m not going to sit here and encourage you to feel guilt about this; I don’t think it will really do anything for you or her or this guy. You’ve already fucked his girlfriend, you’ve already crossed that moral threshold with glee. Even if it were my aim, I can’t make you feel contrite. I do, however, think you might want to examine why it is that you feel so guiltless about this. For most people, it’s a pretty big ethical boundary to cross, no matter how much you like the person you’re crossing it for. If you do decide to look inward, I would encourage you, as much as you can, to exclude her actions from informing your self-judgement. Yes, it’s her relationship with another person; yes, she chose to cheat on her partner. But what role did you play? What does that say about your respect for monogamy in the future? What if that guy were you? I mean, on a basic level, are you ready for a monogamous relationship with someone? (Not that monogamy is the only option for serious relationships! I just don’t know how you could handle non-monogamy at this point because it requires EXTRA honesty).

I know I’m being rude. I know I am. And it’s not because I think that you’re evil for sleeping with someone who has a partner. A lot of people have done what you’re doing. You’re not damned or irredeemable. But you are engaged in something that’s harming another person, and you don’t seem to care. And that is, at a base level, worrisome.

On top of that, you’re completely ignoring the fact that there is no future with a person who is acting how your affair-partner is acting. There is no honest relationship coming down the pike—she has revealed to you (through your very own entanglement!!) that she cannot sustain a truthful or faithful relationship. (Even if you two were to hypothetically get together and agree on non-monogamy, how would either of you trust one another to be faithful to your agreed upon boundaries?) Additionally, in no way is she showing you that she actually wants a relationship with you. If she did……… she would have it…. because you’re already right there… having sex…and declaring feelings. She can say she wants to be with you until she’s blue in the face. Words are completely unimportant in the face of actions to their direct opposite. It’s like how I say I need to stop spending money and then the next thing I know I’m buying a Danny DeVito fanny pack.

I think there is a tendency in us all—I do not fault you for this in the least—to feel that getting along with someone is a metric for connectedness or romantic love, a sign that this is or ought to be a deeper relationship, when the reality is that a lot of people get along and also like having sex together. I don’t mean to be crude or trite but having fun and sex with someone is a very very very very basic level of building “something” intimate. I’m not trying to diminish it—having fun and sex with someone is one of the most pleasurable experiences on earth for my money—HOWEVER, I don’t think it points to some type of star-crossed fatedness. I think it mostly points to the fact that you two are both horny and lonely, begging someone else to fill you up with something, anything. And you’ve both found another person willing to engage in the theatrics of desire, which is a very good approximation for love in the short-term.

But it does not last. I am telling you now that whatever you have with her will not last, not out of a failing of yours (or hers!) but because the desire you two feel for one another is, I verily believe, predicated on thrill. And thrills do not last. There’s a reason that you don’t want to ride a rollercoaster for hours on end.

If this person wanted a future with you, she would not have moved in with someone else. If she wanted a future with you, she would not be fucking someone else. She would not be in a full actual relationship with another person. She wants a present with you. She also wants a present with someone else. He will have to figure out on his own timeline that she is not fully invested in a relationship with him; that is not your circus and those are decidedly not your monkeys.

My recommendation, unshockingly after my above diatribe, is for you to end it sooner rather than later. To get out as quickly and cleanly as you can, not with unkindness but with decisiveness. And then to stop talking to each other for good. You two do not, despite the fun and sex, bring out the best in one another, even if you do fill a void. Then, if you have done the above, I advise you most strongly to look inward, to actually feel your feelings of loneliness, of grief over a missed youth or perceived missed youth, of bitterness over not being more wanted or wanted by the “right” people (these are just some of the most common reasons people enter into shit like this).

The point is not to get you to arrive at guilt. Guilt is like the penny of emotions: it costs more to make than it is worth. The point is to figure out how you got here, why, what purpose it served, and where the holes are in your emotional well-being. The point is then to see how you can perhaps fill those holes in healthier ways that are not being a cicisbeo to an emotionally duplicitous pseudo-partner.

I know I say all this as if it is easy to walk away and end things with a person who is pure fun and pure emotion—a person who provides excitement in a time where all of us are very short on anything other than the mundane or the horrific. I do not think it will be easy to walk away, but I do think it will grow easier and easier the longer you are in this relationship because this relationship has a shelf life, it will start to rot. The choice you have, the only control you have right now over how much pain you feel is how early and maturely you exit this mess. It’s ok to get it wrong or fuck it up or stay in this too long. My letter is meant more as a warning than an admonishment.

I hope you find all the things you’re looking for, I hope you find happiness and love from someone who is ready—honestly ready!—to reflect back that happiness and love with you. Someone who doesn’t even entertain the idea of going back to an ex or carrying on an affair. I hope you find answers. And I know you’ll find excitement and good sex with someone else; she is not by a mile your only shot at that. Just hopefully it also comes with some level of honesty between you two, some level of commitment to the task at hand—loving one another well.

You’ve got this.

You can submit your own question—or yell at me about how I’m wrong—by emailing me at 1followernodad@substack.com