Is It Ever OK To Date a Friend’s Ex?

Questions you must answer before starting a relationship with a friend's former flame

Dear Monica, My friend and her ex-boyfriend have been broken up for six months. I have always liked him and I think the feeling is mutual. How bad would it be if I accepted a date with him? — B. S., Harleysville

The first thing that I would suggest is to have a frank discussion with your girlfriend. It is possible that she wouldn’t mind. Some women might say, “He’s all yours. Good luck!” However, others may exclaim, “How dare you!” Essentially there are two rules to consider here. The first is the old “all is fair in love and war” adage. The other is that girlfriends stick together and loyalty to a friend comes first. Consider the following questions in helping you make the right decision.

  • Is the relationship with your girlfriend something that you would be willing to risk? Most women are going to react poorly to the idea of a friend dating their ex. Realize that there is potential for ugliness, scorned woman type ugliness. You may never be welcome near her or her group of friends again.
  • Consider the character of a man who would date within the close circle of his ex’s friends. Do you think that the potential exists for this to happen again with him among your circle of friends?
  • What about your own reputation? Will you be viewed in a lesser light among your group? I suspect yes. What woman wants a female around with a history of snapping up her former partners?
  • Really evaluate the nature of your attraction to this man. Is it deeply emotional or just physical? Consider whether his feelings for you are genuine or whether he could be using you to get back at his ex in some way.
  • Do you have any “inside information” about this guy? Do you feel like you know him because of intimate details that your girlfriend has shared?  This could create difficult waters for you to navigate as you grow closer to him.

This man better be something really special to even consider violating codes of girlfriend etiquette. Chances are that you will be closing the door on the friendship with your girlfriend and perhaps be facing the cold shoulders of the circle of women who surround her as well.  Beyond all of this, you will always have that corner of your own psyche wondering if he will one day be winking at your friends as he gets to know them over time. Here is the bottom line: her trash could be your treasure, or he could end up to be your trash as well.  More than likely the end result of this scenario will be a lose-lose situation: no guy and no friend.

Monica Mandell, Ph.D. is the Director of the Philadelphia office of Selective Search, the premiere (off-line) upscale matchmaking firm for the most eligible singles. Please send your questions to: