One of the last things I expected to do in my first week of senior year was share a meal of vegan chicken with my freshman year ex–hookup. And yet, there we were. Maybe I said yes to his DM'ed dinner invitation because I wanted to tell myself I had fully moved on and genuinely cared about how he was doing. Or, maybe (definitely) my self–righteous ass was just bored and wanted to give him shit for working at Google and hoped to get a free meal out of it too (I didn’t). This passive–aggressive curiosity begs the question: is staying friends with an ex mature or masochistic?

Staying friends with a partner I’ve had feelings for is something I've always sort of ruled out for myself. I don’t quite understand how to flip the switch from a relationship to a platonic friendship with someone who knows both the scent of my morning breath and exactly how to make me orgasm. I’m thoroughly impressed by anyone who can translate pillow talk to a coffee chat. But the reality of dating, and especially of dating at Penn, is that you will bump into your exes, and it will happen as you run to your 9 a.m. with eye bags and sweatpants on. 

So maybe for the sake of karma and emotional balance, we should all try to stay friendly with our exes when possible. I like to think one of the best non–resume skills I’ve learned at Penn is how to control my nerves enough to silently smile and wave to an ex in passing without also blabbing out an invitation to get coffee or dinner or any form of further contact. And while there are actually some former partners I will take out my headphones for on Locust Walk, I don’t consider myself to really be friends with any of them.

But college is full of clubs and lab groups and classes that can force you to see your ex far more than you’d like. Sometimes, actual friendship can help ease that awkwardness (and also give you an extra source of help on problem sets). Before you decide on trying to become friends with your ex, however, you should consider your motivations for wanting a friendship in the first place. For example, I think we can all agree that if you still find yourself sexually attracted to that person, that forced friendship will easily turn into a situation where no one wins. And if you’re as competitive as 99.9% of Penn students think they are, then you should also make sure you’re not attempting to be friends with the person just to prove that you “won the breakup” by showing your ex what they lost.

Completely letting go of a relationship is extremely difficult, and there’s usually a temptation to maintain that connection in some form. Though I don’t believe in many rules when it comes to dating, there seems to be a universal acceptance of the post–breakup window before friendship with an ex is possible. There’s no hard and fast rule on how long this period should be, so wait as long as you feel you need to be comfortable before reaching out. Because honestly, being friends with an ex before you’re really ready is like buying a box of Oreos and telling yourself you’ll eat just one. 

For some people, the post–breakup window never ends, and that’s okay. No amount of time will ever want to make me get a drink with my high school ex. But for those of you that healthily move on and feel ready to bring someone back into your life as a friend, I have a few standard words of wisdom to impart.

First, assess why the relationship ended. If the disconnect was sexual, becoming friends might be an easy transition. But if one of you took issue with the other’s character, then a friendship might be more difficult.

Second, if you and your ex mutually decide to try the “let’s be friends” thing, make sure you’re both on the same page, and that your motivations align. A secret mission to get back together implemented under the guise of friendship will never work, and this kind of dishonesty will lead to even more emotional pain for all involved. 

Last, you need to acknowledge the reality that both of you will start seeing new people, and that those new relationships should always be the priority. We have space in our lives for as many people as we want in it, but a new partner should never feel pushed out by an old one as you try to sustain a friendship with your ex. 

Of course, following all of this advice and your own emotional intuition can still result in imperfections. Maybe your ex changed in ways that makes any sort of friendship impossible. Maybe you did too. Now, I don't want to equate avoiding unhealthy relationships with tidying up, but Marie Kondo got it right when she said, “Discard everything that does not spark joy.” 

Even the best and healthiest relationships struggle to translate into perfect friendships, and the tension and ulterior motives that can develop are almost always worth discarding. The transition from intimacy to friendship often requires immense emotional labor and self–awareness, but on the rare occasion that it works, you might have a chance to achieve one of the most honest and understanding friendships of your life.