Karen Fratti
Updated Aug 28, 2017 @ 12:13 pm
Blair and Dan from Gossip Girl
Credit: The CW

Once you get over a breakup and are ready to start dating again, it’s only natural to want to dip your toe into the easiest dating pool possible. Which is, of course, the people you already know. Whether you’ve kindly stayed in touch with your ex’s friends or just happen to swipe right on one when they pop up in a dating app, it’s possible that some of your ex’s friends can seem like plausible mates. But things are always more complicated than they might appear, so there are some real questions you should ask if you want to date your ex’s friend.

First of all, whether or not this is a good idea all depends on the situation with your ex.

Dating a friend of your ex is simpler when your relationship with your ex was one of those casual “let’s just hang out until we don’t want to anymore” things. When it’s a friend of a long-term ex, it can be trickier, especially if you all used to hang out on the regular. They likely know the restaurants you like and some of your Game of Thrones fan theories — they also probably know all the gory details about you and your ex. There are pros and cons to all of these scenarios.

Here are some things to consider before letting your ex’s friend know that you weren’t “joking” when you swiped right on them on Tinder.

1Is your ex OK with it?

Normally, there are only a two people you ever have to consider when you start dating someone new: you and the person you’re starting to date. Who cares about what other people think? But, assuming you actually like and respect your ex, this is one of the times when someone else’s feelings should be considered. It doesn’t have to be the only thing, but you should take stock of the emotional baggage you and your ex are carrying so things don’t get ugly. This is usually solved by being up front with both your ex and their friend and asking. You don’t need permission, but it’s a very mature courtesy call to make.

2Why are they doing it?

Don’t get us wrong: You’re hot, a great catch, and yes, you and your ex’s friend definitely locked eyes over pub trivia that one time. But friendships are complicated. If they’re making a move for you, that means they’re likely OK with the possibility that your ex will ice them out. Maybe they weren’t that close anyway, and everyone’s super chill and unemotional about it — or maybe they’re the kind of person who likes sneaking around with their best friend’s ex after a breakup.

3Are you cool with worlds colliding?

Speaking of sneaking around, if you’re already banging your ex’s best friend and being secretive about it, you’re going to have to address that eventually. Is it because your new boo didn’t have a grown-ass conversation with their friend and float the idea by them? Or is this like a Blair and Dan Gossip Girl situation, where it’s just easier if no one else knows until it all blows up in your face? If things really are crazy relaxed and no one’s breaking any Friend Code, can you all set boundaries when worlds collide?

4Are you just being super lazy about finding someone new?

You loved or at least liked your ex, so it makes sense that you vibe with their friends. But sometimes the best thing you can do after a break up is to totally switch things up. Is this person date-able simply because they’re already at your local happy hour spot? Dating new people can be dreadfully hard, we get it, but branching out is a good thing. If you’re digging your ex’s friend, try to take this relationship slow and really feel it out. Maybe date other people on the side just to make sure you’re being totally fair to yourself and taking advantage of all the options.

5What do you like about them?

Their social proximity, dreamy eyes, and the ease of already having access to the Instagram profile aside, why this person? At the risk of stating the obvious, people who are friends usually have a ton of things in common, including personality traits. If something in particular wasn’t working with you and your ex, make sure you control for that factor before falling head over heels with their best friend.

6Are you doing it to stay close to your ex?

Even if you’re not doing it consciously, watch yourself. Don’t use an ex’s best friend as some half-assed ploy to win someone back, stay in their world, or make them jealous. Or do! It’s your life, do whatever you want, but be prepared for the consequences. If it’s meant to be, it’ll happen.