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Dating a Friend’s Ex: Is it Ever Okay?

It started our innocently enough. Brian had been divorced for three years when he filled out the cumbersome eHarmony profile. Looking through all the profiles on other dating sites was daunting, so he decided to let a computer do the mate selection for him. He had a good feeling about this, and as luck would have it, his instincts were on target. Among the matches eHarmony’s algorithms presented him with, he discovered Angie, a beautiful and intelligent woman who shared many of his passions. However, the match had an unexpected complication: Angie had been married to a long-ago friend of Brian’s. Nevertheless, Brian thought about it and decided to contact Angie anyway. After some initial hesitation for the same reason, Angie agreed to go out with him, and their first date led to a delightful courtship that culminated in marriage. Although the couple couldn’t be happier today, they pissed off a few folks along the way. Apparently Angie’s divorce was not an amicable one, and her ex was infuriated with both of them.

After hearing this story (and numerous others like it), I thought about Brian and Angie’s situation,

and my deliberation led me to flesh out the question “Is it ever okay after a divorce to date a friend’s ex?” It’s a complicated issue, and every situation is different, but I do have some insights and thoughts I’d like to share.

There is a good chance that when you start dating, no matter where you live, you will come across some potential candidates that you are already acquainted with. People you know might pleasantly surprise you by asking you out. And some of those folks may have previously been wed to a person you are familiar or even friendly with.

In a small town, there is a strong possibility that you know many of the divorced singles living there already. That being the case, there is a high probability that you may be asked out by someone who was once married to a friend, acquaintance, colleague, or even a relative. Or, on the other hand, you might be the one doing the asking out. While this might make for some awkward conversation in the beginning, it doesn’t have to be a deal-breaker.

The same thing can happen even if you live in a large city. Several of my divorced friends in New York City, where I live, described to me that over the years they have been matched up (through introductions, internet dating sites, and serendipity) with potential partners who were once married to someone they knew. A woman I’m acquainted with is happily married to the ex husband of a former friend of hers. She told me that she met him and his wife because their children once attended the same school. She ran into him at a political event years later when they were both divorced. They started dating shortly thereafter.

None of this sounds awful or insurmountable, right? I believe that life does not have to end with a divorce, and if you want to fall in love again, you can. So what happens if the person you are interested in dating, or are falling in love with, was formerly married to a friend? How do you negotiate these potentially rocky waters?

Hypothetically these couplings could work out very well if you proceed with extreme caution and follow some guidelines.

First, I suggest assessing the quality of the friendship you currently have with the person’s ex. In my opinion, the exes of best friends or really good friends are completely off limits. Use your moral compass to guide you. Why cause pain to someone you care about and who cares about you in return? Good friendships are sacrosanct. No one needs this level of drama; life is complex enough.

I also suggest honestly asking yourself, “How would I feel if a friend of mine was dating my ex?” In other words, where would you feel comfortable having the line drawn? I asked quite a few people this question, and most said they would be okay if their ex was dating an acquaintance. Everyone said they’d be terribly upset if it was a good friend. One person figuratively commented, “It’s okay if someone near my home dated my ex, but not too close to home.” I think this sentiment makes a lot of sense.

Now that we’ve established that it is not okay to date the ex of a best or even good friend, let’s discuss acquaintances. If you’ve decided after careful deliberation that it is okay to date the ex of an acquaintance, move forward with care. Please remember that feelings can easily be hurt on all sides. Consider taking the high road by addressing the situation directly with the acquaintance prior to getting involved with their ex. (As well as, obviously, addressing the situation directly with the person you want to be dating.)

In the case of Brian and Angie, Brian did call his old friend to communicate his intentions. In their particular circumstances, Angie had been divorced for five years and Brian had not spoken to his old friend in over a decade. The men had been colleagues once, but that was many years back. Still, after weighing the costs versus the benefits, Brian decided calling was the “right thing to do.” The conversation didn’t go particularly well, but Brian had prepared himself and decided that he was willing to risk the possible social backlash by getting involved with Angie. I think if you give someone the respect of contacting them, no matter what their reaction is, you could feel that you did the appropriate thing, and that may ease your journey.

Probably the cleanest and least complex scenario is that you date someone where there is no crossover of social circles. But in today’s E-world, there is a good chance that you may run into someone that you’d like to date and you happen to know their ex. At least now you’ll be prepared.

Please note that all names in this post have been changed to protect the privacy of individuals.





  • Mark

    Greetings,

    I came across your post while doing a search on dating a friend's ex. My search was not for moralistic reasons but more on the terms of approach. To my surprise I found mostly high-minded rhetoric admonishing men about the "bro-code" and likewise women saying it was offensive and off limits.

    While your posting is more pragmatic, it still seems based in great degree on the off-limits nature of someone else's past relationship. I find this to be incredibly short sighted and controlling. If there is a mutual attraction between two adults the issue is between them alone to decide whether they wish to pursue a relationship. There is no need to seek assurance or permission or any other type of justification from former lovers or spouses.

    I certainly understand that if there is still contact with other members of the relationship that they would need to know and that it might need to be approached with a certain level of consideration but certainly not in the sense of seeking approval. The issues of mutual friends, children, families may all bring pressure to the new relationship but that is not unique and is solely the decision of the potential lovers to decide if these are waters they wish to navigate.

    Regards,
    Mark