Difficult Terrain Ahead: When you date a friend’s ex

Difficult Terrain Ahead: When you date a friend’s ex

I recently coached a client who is dating her friend’s ex. She came to me very confused as to how she should even begin to open the lines of communication with her friend so that she didn’t cause ‘irreversible damage’ with their relationship and also within her community.

While she really wasn’t doing anything technically wrong — after all, one woman’s weed in her garden is another’s flower — she did feel badly that somehow the relationship would be frowned upon due to societal views and that she’d be shunned for committing girl code betrayal (which, BTW, in many ways it is).

It was a true dilemma for her and she really couldn’t come to any resolution that made sense.

She didn’t plan it this way. She didn’t even seek it out. It just sort of happened. She was into it, he was into it, there was serious chemistry, and she thinks she may have stumbled upon something really special.

Yet …

She told me that she lived in a small community where finding new love and a suitable partner was challenging. But she really didn’t want to end her friendship with her close friend.

So, what is the proper protocol when you fall for your friend’s ex?

Or, better put, have sex with an ex.

I guess the first question that needs answering is whether or not the “juice is even worth the squeeze” —is it even worth telling your friend that you’ve just exchanged pleasantries across enemy lines?

I mean, really, is it even justifiable to tell your friend?

Let’s be clear here: Permission isn’t necessary.


This is where you come to a crossroad about what’s more important — a roll in the hay or your friendship? Walking away from someone who could end up being the love of your life, or putting one of your friendships in jeopardy and looking like a traitor?

Ugh … the eternal conundrum.

The truth is, nobody really knows where a new relationship is going to go and chances are it might not even make it out of the bedroom.

But …

If, in fact, real feelings start to develop, how you choose to handle this delicate situation speaks far more about your character than the impending love bug bite that’s starting to itch.

The advice I gave to my client was rather straightforward and is pretty much the way I run my life in general, regarding all matters.

Even the delicate ones.

My father taught me long ago that honesty, while often not easy, is consistently the best policy.

And while some people will not be very happy about certain truths being told, being open and honest seems to have a much longer shelf life than a salacious story being told around town. Long after the dust settles, in any given situation, one’s character and how they choose to handle certain situations seems to be what’s remembered most about them.

I urged my client to call up her friend (who, alas, will most likely not be a friend after their chat) and tell her right away — before she hears it on her own — that she is dating her ex.

I encouraged her to be truthful and tell her that she had developed real feelings for this man and would like to continue to see where it goes. And that while it might be hurtful, she understands that their friendship may not be able to continue, but that she respects her and hopes they can find some common ground to work with.

And BTW, let’s not blow smoke up anyone’s backside here.

No matter what is really said, chances are this chat isn’t going to change how the friend responds going forward.

But …

Are you going to be friends after this?

Probably not.

Are you going to have a few things to overcome in the community?

Probably yes.

Will the situation blow over eventually?

Most likely.

Were you honest about it?


And nobody can ever take that away.

In the end, some will say if you date a friend’s ex then you were never a friend to begin with. Others will say that the people who want to stay in your life will always find a way back in.

My personal feeling is that it really depends on the degree of friendship you have and the level of feelings your friend has for their ex. But if they feel little, are more of an acquaintance than a true bestie, and have a good relationship with their ex, it can sometimes work out for everyone.

No matter what the situation is, honesty is always the path to take.

Because in the end, you can apologize for being wrong — but you never have to apologize for being honest.

Until next week,



Born and raised in Bloomfield Hills, Michigan, Karin has a BA in sociology, with a minor in psychology earning honors at Michigan State University along with certification in relationship and grief coaching. She is currently accepting coaching clients and can be reached @[email protected] for a free consultation.

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