How to go about dating your friend’s ex without feeling like an awful person

You know that scene in Mean Girls when Gretchen Wieners explains to Cady Heron why it would be absolutely unacceptable to date Aaron Samuels? “Ex-boyfriends are off-limits to friends,” she says—nay, screeches. “That’s like the rules of feminism!” I’ve often thought about that scene (and not just in light of Gretchen’s…creative understanding of feminism), wondering whether the spirit of her statement might hold some merit. Is it true that dating a friend’s ex would be ill-advised?

It does, after all, seem like a hard line to draw in the sand. Abiding by the principle means cutting off the potential to be with a person before you’ve explored whether or not there’s a romantic spark. On the flip side, it might also impact your relationship with your friend, depending on things like how they broke up, how long they dated, and whether or not they still harbor feelings for this person in question.

“You can date whomever you’d like, but it’s likely that you’ll want to consider your friend’s feelings too,” says sexologist Jess O’Reilly, PhD. If the breakup was recent, for example, your friend may have some lingering feelings. They may also feel awkward about situations in which the three of you might hang out after these new relationship lines are drawn. Or they could simply hate this person from their past, whom you’re now curious about (hey, some breakups are especially painful). And in that case, your friend may not want you to have anything to do with the ex—to save you from future anguish.

Before knowing the best way to proceed, you need to get to the bottom of these feelings. The worst way to go about this? Assuming you know how your pal might react. “The best way to approach this involves an open, honest conversation,” Dr. O’Reilly says. So don’t beat around the bush or ask hypothetical questions. Instead be clear and direct, which means you need to admit your feelings outright—before things go too far with the ex.

“When you make assumptions about your friend’s feelings, they’re more likely to feel stifled and less likely to be honest about how they feel.” — sexologist Jess O’Reilly, PhD

“Ask your friend how they feel, and be sure to ask neutral questions as opposed to leading ones,” Dr. O’Reilly says. So instead of saying something like, You don’t mind, right? You guys were never serious, she suggests an approach that provides your pal some agency. It seems like something has been growing between me and Kevin, and I wanted to talk to you before things went further. How would you feel if he and I started to see one another?, is a better approach.

“When you make assumptions about your friend’s feelings, they’re more likely to feel stifled and less likely to be honest about how they feel,” Dr. O’Reilly says. If your friend asks for time to think about it,  give them that—but ask for a deadline. This will help make sure that you actually get a response, rather than your friend just biding time to avoid the situation entirely—which, PS, isn’t fair to you.

Ultimately, your friend may be completely cool with you exploring a relationship with their ex. Or, they may say that they wouldn’t be comfortable with it. Getting the latter response doesn’t mean you’re romantically sunk; it just means that you have to evaluate which relationship means more to you. “It’s your choice as to how you proceed,” Dr. O’Reilly says. And if your friend’s prerogative is a them-or-me ultimatum, you need to respect that too.

I know that this isn’t exactly the most satisfying answer, but it’s the most realistic one. All you can do is collect as much information as possible from your friend about how they feel and then make the best call from there. As long as you’re comfortable with your highly informed decision, you’ve made the right choice.

Have a crush on your BFF’s current S.O.? Here are tips about how to proceed. And if the friendship ends up being collateral damage, it won’t necessarily be that way forever.