A Guide To Dating A Friend’s Ex

One of my favorite shows when I was younger was the American TV series, “Gossip Girl.” It wasn’t relatable to me, but it was entertaining. One of the aspects that made it unrelatable is how incestuous the characters were. They had taken such a zero grazing approach to relationships and sexual escapades. It just wasn’t real life. How was it possible that they’ve all slept with each other? Was their world that small?

Well, I realized that TV could, easily, be real life. I recently went through two heartbreaks: one from a friend and the other from a man. To cut a long story short, she was my housemate and friend, and dare I say, confidant. The one I would go to when I had any issues and the unbiased party between the man and me when we had problems. And even when we finally ended it, she was his and my advisor, or so I thought. So it was a real punch in the gut when I accidentally found out that they were sleeping together behind my back barely a month after we stopped seeing each other, and literally within weeks after she ended her relationship. The kicker is that, ironically, we had sworn that we would never sleep with each other’s former flames a month before I found out because someone else had done something similar, which got us talking. But, such is life. It throws some major curve balls sometimes.

The general ordeal got me thinking about several things. One of them is, is it acceptable to start dating a close friend’s ex? Despite it being morally wrong, logically, I don’t think it’s black and white. I do believe there are some circumstances that kind of make sense to start dating your friend’s ex. Generally, it’s a bad idea, but if you’re just itching for it, I feel that there is a right way to go about it.

Be Honest

Be honest not only with yourself but with your friend, too. Are you doing it just to get your boat rocked or are you honestly into the guy/girl? If the roles were reversed, would you be supportive of this? I know that life’s motto these days is “F*ck everyone else, do what makes you happy.” But as humans, unlike other mammals, we have the gift of rationality. We can analyze situations logically before we take action. Otherwise, we’d all be a pack of wild animals. Have an honest conversation with yourself and then with your friend before you proceed with the relationship. The friend may be upset in the beginning, but they will value your honesty, and your friendship may even continue.

Give It Time

Emotions take a while to heal. How long has it been since they ended things? Are they still in touch? If your friend was into the ex, chances are even if they’ve moved on, there are still some lingering feelings. As a friend, you should take some time between the breakup and you hooking up with the ex. It’s not only respectful, but it also gives you and the ex the time to evaluate if what you feel for each other is worth it or not. If it’s been a few months, or even better, years, both parties have moved on, and you’re pretty sure this is the person you want to be with, give it a go.

Identify The Motive

Just as people can be good, they can also be evil. Ying and yang. Try to be clear on the real intention of the ex wanting to get it on with you. Did they initially have a chance to be with you before they hooked up with your friend and didn’t, which was the case in my situation? If so, why now? People can be sleazy and devious and they may be using you to either take revenge, disrespect your friend, or for an ego stroke. For example, in my case, the street cred of having slept with friends. Don’t allow yourself to be a pawn in this type of game. It’s twisted.

Own It

Ideally, you shouldn’t have to get caught in a lie. But if you are caught in deception, fess up. Don’t act like a victim or try to make your friend seem irrational. Also, I believe in being yourself. If you’re “that” kind of person, own it. Be yourself. Don’t pretend to be someone you’re not. There is beauty in being authentic. Authentic bad is always better than fake good. We cannot all have the same values in life, and no one should impose similar values on you. Let’s leave that to religion. Consequently, be ready for the consequences of your choices.


Love hits you when you least expect it. You never know when and who you will find it with. One man’s poison ivy is another man’s spinach. If you have to do it, be an adult about it by being honest about your feelings early on. It prevents any unnecessary drama. Also, no one can dictate who you can and cannot be with. But, there are simpler ways to handle issues in life. A proactive approach of clear and honest communication, thoughtfulness, and consideration are all critical to ensuring a smooth segue into your situation. If you just have to hook up or date a friend’s ex, go about it the right way.

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