“Did you just check out my ex?”

I remember the day well. I was standing on the side of the football field watching my eight-year-old son battle it out on the first day of hitting at football practice. My girlfriend (a single mom) looked over at my 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. He’s really hot.”

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:

• Willingness to broach the subject: Good friends have each other’s back; they don’t blindside them with a secret relationship. A conversation with your friend before pursuing the ex shows respect for the friendship and consideration of their feelings. If you can’t have that conversation, that’s a sign that dating the ex is a no-no.
• Depth of friendship: Is the person the ex of a casual friendship or a bestie? True friendships are hard to come by and not something to take lightly. If it’s someone you aren’t close with, you may not be as concerned about drifting apart due to dating their ex. But if it’s a close friend, you might want to think twice.
• Time frame of the break-up: How long has the relationship been over? If it’s been years (like a high school relationship) it might 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.
• Status of the ex-relationship: Did the relationship with the ex end on good terms? Is it contentious? Are they in a bitter battle for child custody or support or was it a mutual breakup? If the pain of the breakup is long gone and emotions are stable, your friend might even recommend their ex to you as a better personality fit.
• Emotional health of 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.
• Nature of the attraction: Why do you want to date your friend’s ex? What is it about them that you specifically find attractive? 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? Make sure you’re interested in this person for the right reasons.

Before asking for the ex’s number, search your heart, pray about it and make sure your intentions are above board. Give yourself time to process your feelings and live in the tension of the crush for a while. If the attraction is still there, approach your friend and ask for a blessing to pursue the relationship knowing with eyes wide open there could be a cost to your friendship, despite your best intentions.