Is it ever OK to fall in love with someone who's been on a relationship with a close friend or coworker?

Is It Ever OK To Date Your Friend’s Ex?

Summer K

Dating can be tricky at best. Dating when it involves the social minefields of love gone wrong can be even more stressful. While we’d like to think most people have the option of dipping their toes into a new pond, when it comes to mating and dating on this small island we call Manhattan, let’s just say things can sometimes become dicey at best.

You see, here everyone knows someone, and you’re really only six degrees separated from the last person you took home for the night. In a city driven by shared ambitions and social circles woven together by careers, college friendships and similar interests, it’s only a matter of time before you stumble into this dilemma. So how do you handle that lingering spark of attraction when the perfect person is presented to you in a not-so-perfect scenario?

Here’s some guidelines we think everybody should be following — in NYC and beyond:

1. Dating Someone Who Dated A Close Friend For More Than Six Months (Recently)

Quite simply, DON’T do it. You know too much, you saw too much and no good will ever come from this. No matter how much you desire this person, you will cause a rift that will most likely never be healed. This is even more serious if said couple lived together. By pursuing this person, you’re basically saying you have no respect for your friend or the relationship this person had with their former significant other. It will also cause issue within your friendship circle and force people to choose sides in the same way an ugly divorce can and does. Yes, you may be gaining a new boyfriend or girlfriend, but are you willing to hedge that against your nearest and dearest? We say it’s not a gamble worth taking.

2. Dating Someone Who Dated A Close Friend Casually

Possible, but tricky. This must be discussed with your friend in person — after all, you owe them that courtesy. If he or she was the one that ended things, it shouldn’t be a problem (though it might be a little awkward at first). If they were the one that was kicked to the curb and they still give you the greenlight, be courteous (as in don’t rub it in their face by attending the same events they do) and cautious. Just remember, if this person you want to date was less-than-honorable in their approach to dating your friend, it could mean you’re the next notch on his or her bedpost.

3. Dating Someone Who Dated A Friend Of A Friend

Look, you’re not really going to feel the heat on this one, but your friend could, so take it REALLY slow. Obviously you might end up at the same social functions together, so make it a point to reel in your impulse to be all lovey-dovey or sequester yourselves in the corner. Given the degree of separation, you’re not required to make this a bigger deal than it is, but it should be noted that you owe it to yourself to be respectful of this past relationship and not act like it never existed.

4. Dating Someone Who Dated A Coworker

Office stress can really be compounded when you’re dealing with an angry coworker or supervisor who doesn’t appreciate the fact that you’ve taken up with their ex. The same rules above apply to this scenario as well. Ask yourself if the person you’re interested in is really worth it and decide if being with them truly does outweigh the cons. (Also, if this gets serious and you ARE facing some office backlash, it might be time to explore a new job opportunity if the relationship appears to have credible staying power.)

5. Dating Someone Who Dated A Friend Or Acquaintance In College OR High School

Let’s preface this for a moment. This ONLY applies if we’re not talking about your BFF and you weren’t there when the breakup went down. Otherwise it’s water under the bridge, folks. If you’re even five years past graduation AND this relationship is history (meaning everyone’s moved on and is off doing their own thing), it’s your friend that needs to get over it — not you. People grow and change, and you can’t be expected to put your life on hold just because a pal is still bitter because he or she got dumped right before prom or that big fraternity pinning ceremony. (And we say this having been in the position where one of our friends dated an ex, and yes, we were completely fine with it.)


Have you ever been placed in this situation before? Share your thoughts in the comments section below or sign up and post a question in our advice section now!