It would be great if there were an unlimited supply of eligible singles at your school.  But the reality is, social circles aren’t that big, and the potential for dating overlap is huge.  So what do you do if you find yourself falling for a friend’s ex?  Before your do anything, consider the following:

How long has it been over.  It’s one thing if your friend and his or her ex broke up a long time ago.  It’s quite another if your friend is still getting over the relationship, and is still visibly upset when they talk about it.  If the wound is still fresh, getting involved with your friend’s ex is a bad idea.

Who broke up with who.  When you get dumped, it hurts your ego—I don’t care how confident you are. If you get involved with the ex of a friend, and it was your friend that got dumped, it sets your friendship up for a strange dynamic.  Very likely, your friend may feel jealous and start thinking “what do you have that I don’t.”  And that kind of thinking will definitely cause tension in your relationship.  If, on the other hand, it was your friend who decided to call it quits, you might be in the clear.

Is it worth damaging the friendship over.  This is the number one most important thing to consider when contemplating hooking up with a friend’s ex.  The reality is, even if your friend says it’s okay, seeing the two of you together might make your friend feel betrayed or like they can’t trust you.  So consider long and hard if this crush you’re having is worth possibly losing a friend over.

Would your friend do this to you.  Quite simply, some friends are better friends than others.  There are probably people you’re friends with who, at the end of the day, will always look out for themselves.  There are probably other friends of yours who are fiercely loyal, who will always stand up for you, and who would never do anything that might hurt you or your friendship.  Friends like that can be hard to come by.  And if the ex you like belongs to one of those friends, you might want to reconsider.

Consider testing the waters.  Before you do anything, think about talking to your friend about your situation and seeing what his or her reaction is.  Their reaction might be way better or way worse than you expect.  But only by knowing their thoughts on the matter do you have a true grasp on how much you’re risking to pursue this relationship.

If you’ve decided that you’re going to go for it, the most important thing you can do to salvage the friendship is to tell your friend first.  The sketchier you act about it, the worse it is.  And if your friend feels like you lied AND you’re dating their ex, you will certainly lose your friend’s trust.  You have a much better chance of things going smoothly if instead you come clean starting with, “I care about you and our friendship and I want to be honest with you."
 

Amber Madison has been writing about sex, love, and relationships since college (she went to Tufts University) when she wrote for her school newspaper's sex ed column. Since graduating, she's published two books: Hooking Up: A Girl's All-Out Guide to Sex and Sexuality and Talking Sex With Your Kids and has been quoted in a ton of different media outlets from Seventeen magazine to MTV to NPR. Have a question for Amber? Send us an email!