How to (Tastefully) Date Your Friend's Ex

Couple sits on park bench while jealous friend watches

Pat Benatar alerted the nation of the state of love when she compared it to the heavy artillery and dirty bombs one faces in a war. But do you think the idea of my body being metaphorically blown to smithereens stopped me from dating not one, but two (yeah...) of my best friend's ex-girlfriends?

Indeed, it did not.

But this isn't about Peter (fake name), Jessica (fake name), or even Mothra Blurgenstein (shockingly, actual name -- kidding!) It’s about what I didn't do and, more importantly, what people should do when pursuing the exes of their best friends, or less-than-best friends, even. From the lips of relationship fuck-ups and our resident sex sociologist, Dr. Chauntelle Tibbals, here is what you should and shouldn't do while dating the ex of a friend.

A couple walks down the road as a jealous friend follows

Assess the situation

What kind of ex are we talking about here? Did they date for a week in eighth grade and break up via AIM? Have they been together for 10 years and just ended things in an emotionally draining way? Assess the situation by putting yourself in their shoes and thinking about how you would react if the situation was flipped.

"The thing to remember is to be open about your feelings", says Dr. Tibbals. "Though you always run the risk of hurting others, no good ever comes from keeping secrets in these types of situations. It’s also important to remember the evolving power of social norms. Your friend may be OK with what’s happening at one point, but their feelings may change."

I went for my best friend's first ex-girlfriend a day after they broke up. Suffice it to say, neither one of them was over it. Yikes. Sorry, Peter, I was very much the asshole in the situation.

Ask yourself if it's worth it

Seriously, what is it about him or her that's worth potentially ending a friendship over? Is it just a physical thing? Do you think you two actually have a future together? Don't risk everything for the possibility of piping-hot sex. Sex is fantastic and all, but there are so many other people (who haven’t seen your best friend naked) who will gladly sleep with you.

"Are you romanticizing the person?" asks Dr. Tibbals. "Are you making them out to be an idealized version of what they truly are? Is there actually something there? Let an honest assessment of your feelings factor into how you decide to proceed.

"People often idealize things they only see in ‘highlight reel’ form. Your friend's partner may seem awesome on a Saturday night when that's all you see of them, but a true connection (regardless of how you met) is always tougher to find. The best thing is to be honest with yourself regarding the nature of your feelings. Are you just looking to bang?"

The reason I went after TWO of my BFF's ex-girlfriends is that I really believed I would make a good match with both women. Having so many shared interests made it seem like we would make a terrific couple. That being said, the first relationship I pursued was not worth it, because I didn't take the time to think if dating my best friend's ex would ruin our friendship.

The second time was fine, because neither of us liked the girl that much.  

Couple in a park with a pervert watching them behind a tree

Consult your friend first

Before you go sticking your tongue in stray orifices (like her face, ya pervert) talk to your friend and tell him how you feel. Take solace in the fact that there's no conceivable way it can not be awkward.

"Directly!" chimes in the good doc. "Ask directly, say the words. Inferring, by definition, leaves room for interpretation. Even if it may be uncomfortable, make your desires and intentions known. Though this might not solve everything, it's a good first step."

Objectively, it's a weird thing to go after someone who definitely had sex with your best friend. Eskimo brother be damned! Wait, is it still kosher to use the term "Eskimo"? Wait, is it still kosher to use the term "kosher" when not talking about food blessed by a rabbi?!

Think of the conversation as a PowerPoint presentation. Walk them through your feelings, explain your intentions, and really try to convey that you're not just looking for sex and legitimately can fall in love. Still... tread very, very lightly and acknowledge that what you're doing is a huge social faux pas.

Follow your friend's advice closely

So, maybe your friend is kinda cool with it, but has some reservations. Whatever you do, do not ignore those reservations. If he’s over her, but will need a few months to be fine with the concept of you two as a couple, try your hardest to give him space.

If seeing you two kiss or show affection is going to give him some kind of mental breakdown, figure out a plan to make it work -- pending he gives the OK for you two to date.

Don't flaunt your love

Even if your friend claims to not care about witnessing affection, make a point to tone it down while around him. There's nothing wrong with holding hands or kissing, but reconsider going into a full-on dry-hump session while you're all sitting on the couch together watching Waterworld.

Don't go behind their back

We're saving the best for last, except this one is "best" in the sense that it’s the best way you’ll get excommunicated by your group of friends forever if you do it. Don't mess around with your friend's ex behind his back. That's a shitty thing to do and they will almost always, inevitably, find out.

"This is the only answer that's simple," says Dr. Tibbals. "No. Never."

Sign up here for our daily Thrillist email, and get your fix of the best in food/drink/fun.

Jeremy Glass is a writer for Thrillist and has finally learned his lesson.