Is it Ever Ok to Date a Friend’s Ex?

I remember the day well.  I was standing on the side of the football field watching my seven old son battle it out on the first day of hitting at football practice.

My girlfriend (a single mom) looked over at my brand new ex-husband who was coaching the boys, then glanced at me at me and sighed wistfully.  “You know, if he wasn’t your ex-husband I wouldn’t mind going out with him.”

Huh?  Awkward!

I gave her “the look” and my friend wisely chose to zip it and never bring it up again.

But in a world of broken marriages and relationships, these questions come up all too often.

Is it ever acceptable to date a friend’s ex?

Every situation is different, but here are some considerations to keep in mind…

  • How close is your relationship with the friend?  Are you willing to risk tension?  Good friends have each other’s back… they don’t blind side them with a secret relationship.  Having a conversation with your friend before pursuing the ex shows respect for the friendship and consideration of their feelings.  It also shows maturity.
  • How long has the relationship been over?  If it’s been years (like a high school relationship) it may not be a big deal, but if the divorce or break-up is painfully fresh, you may want to reconsider opening this can of worms.
  • Did the relationship with the ex end on good terms?  If your friend dated in an honorable fashion and the pain of the breakup is minimal, they might even recommend their ex to you as a better personality fit. 
  • How healthy is the ex?  What were the reasons they decided to end the relationship?  Do your homework.  If addictions, abuse, adultery or serious character defects caused the breakup, then stay far away from the charming train-wreck.  You were warned.
  • Would your friend cringe if you got married?  Could you hang out with your friend without it being too uncomfortable? Would she poison his popcorn if you came over for a Super Bowl shindig?
  • Ask yourself why you want to date them?  Is it because there is a true relational spark (beyond the physical) and you can’t help yourself, or is it possible you are passively getting back at your friend for an unspoken hurt or disappointment? Search your heart, pray about it and make sure YOUR intentions are above-board.

In more recent years, two of my girlfriends chose to date an ex-boyfriend of mine(strangely enough…the same guy).  But because we were all on good terms, it never became an issue and the friendships have stayed strong even though both of the women ultimately decided to end the relationship. 

What do you think about dating a friend’s ex?

Photo Source: heartit.com via Lisa on Pinterest

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