By Corey Mueller
The Chicago Tribune asks relationship expert Susan Winter for her advice on how to deal with your ex’s flirtatious friend.

Q: You’ve broken up with your partner but still stay in contact with his or her friends. What do you do when your ex’s friend starts flirting with you?

“If you live in a remote village of 100 residents, having your ex’s friend flirt with you may be a welcome prelude to romance. For the rest of us, this option is courting danger.

Online dating offers an endless selection of new partners, as does dating from your own extended circle of friends. Encouraging the friend of your ex is both messy and unimaginative. Rarely can this type of interaction occur without collateral damage.

A warmly stated response of appreciation (but no interest) works well in this case:

“John, we’ve had wonderful times together in the past. But this is too close to home to be comfortable. You’re a great guy — but this isn’t a possibility for me.”

This type of comment is gracious and to the point, leaving no confusion as to the firmness of your position. It preserves the other person’s ego. It saves any fallout from your ex, his or her family and friends. And it leaves you looking appreciative, but rational and grounded.

A politely crafted exit is always a winning move to make.

— Susan Winter, relationship expert and love coach

If it makes you uncomfortable or you think it’s inappropriate, say so and ask him or her to stop.

If you want to, flirt back. It might be harmless, and it may not mean the other person is interested. Some people are charming and enjoy flirting. Give it time to see if it’s an isolated incident or if it does mean he or she is interested in pursuing something more.

If there clearly is interest in going out on a date, have a conversation about what this means regarding your ex. Variables such as whether or not you stay in touch with your ex and how close their friendship is are important to take into consideration. Does your ex know, and/or would you tell your ex? Would this person lose the friendship with your ex if this new relationship was found out? Talk about what social situations would be like, particularly if the three of you still share mutual friends. Discuss whether or not you would want to get your ex’s “approval” before turning the flirting into something more.

— Anita A. Chlipala, licensed marriage and family therapist, and author of “First Comes Us: The Busy Couple’s Guide to Lasting Love”

Social Graces is a series asking two experts for advice on awkward situations. Responses are edited for space and clarity.

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