Couples Advice

One of the most awkward romantic situations which you can get into is dating a friend’s ex. This places you squarely between two people who you care a great deal about and who may actually hate each other. Does this mean you shouldn’t do it? Not necessarily, but be prepared to proceed with caution.

Denise from Point of Rocks, MD writes:
“My best friend recently broke up with her boyfriend, and it was a pretty bad breakup. In spite of this, I’ve been unable to take sides. I can understand the breakup from my friend’s perspective and also from her ex boyfriend’s perspective—and what’s more, I’m attracted to my friend’s ex and I think I want to date him. But I think my friend will hate me if I do. What do I do?”

Hi Denise. This is indeed an awkward situation, though I don’t think you should assume your friend will hate you for dating her ex. If you respect both these people as much as you say you do, they must have earned that respect. In that case, you can respect them again by allowing them to be mature adults about your decision. Give your friend a chance to co-exist with you harmoniously and to accept your choice to date her ex before you decide not to make that choice for her sake.

It seems clear that you’ll be unable, at least for the time being, to explain to your friend why you don’t blame her ex for what happened. But you can be sympathetic (I’m assuming you must have been up to this point, since your friend isn’t mad at you now), and let your friend know that her feelings are as important to you as her ex’s feelings are. You can explain to your friend that you wouldn’t necessarily be considering dating her ex if you didn’t trust your friend to understand your feelings in return and to support you. In this way you turn your desire to date your friend’s ex into a compliment to her.

If your friend doesn’t accept your decision, you’ll be faced with a hard choice—and that’s not one which anyone can give you advice on making, except to be true to your heart. Many people have lost what would have been a lifelong best friend over a momentary romantic fling; then again, many people have lost the chance for a long-term romantic relationship over a friendship which wasn’t meant to last. You have to ask yourself which relationship has greater long term viability and will make you happiest in the long run if you’re forced to make a choice. You might also want to take a closer look at why you’re being forced to make that choice. It could reflect on one or both of your friends, or on you. This in itself may influence your choice.

Also consider that if you delay a bit, your friend and your ex may stop hating each other as vehemently, or gain new perspective on their situations, eliminating the entire difficulty. You also may have an easier time figuring out whether your own feelings for your friend’s ex are worth causing your friend the emotional difficulty of accepting them. There’s really no rush, and introducing instability into an already difficult situation isn’t necessarily a kindness to anyone involved and can be quite inappropriate. Giving everyone some space is itself an act of compassion which your friend and her ex may both appreciate. Hasty decisions are often foolish ones.

Just don’t forget that it’s possible that everything might work out—if you turn away from this situation because you assume that it can’t, you will be responsible for why it didn’t, not your friend, and not your friend’s ex. You may not be forced to choose between them at all; the mature thing to do is to give others the chance to be mature.