What To Do If You Have Feelings For Your Friend’s Ex

Pin it

Editor’s note: Have a dating/sex/relationships conundrum?Email us at thedatereport at or fill out this anonymous form, and one of our experts will help you solve it.

I am really interested in a guy, however, my friend used to date him. It’s been a year but I still wonder if it is the right thing to do or not.  I fear it could cause problems with my friend.  What should I do?

Plus: What The Couples Of “The Office” Taught Us About Love

It isn’t surprising that you’re taking an interest in the same guy your friend once dated. Keep in mind, we often have similar tastes and share views on a range of subjects as our friends, so this does happen from time to time.

The worst case scenario is you lose your friendship with your friend and it doesn’t work out with the guy, either. Obviously, the best case scenario is you maintain your friendship and everything works out great with her ex, too. Is this potential love interest worth potentially losing a friend over?

Plus: I Date Outside My Race Because My Race Doesn’t Want To Date Me

Before you make a move, make sure you do the following:

  1. Make sure they are broken up and he truly is her ex.  Sometimes people take a temporary hiatus and come back together.  You wouldn’t want to interfere with that.
  2. Allow ample time for both of them to process their relationship and grow from it.  If your friend has moved on, then that might be a good indicator that enough time has passed.
  3. Prepare for your friendship to change.  Even though they might be cleanly apart, sex tends to bring up issues and conversation with your friend might feel awkward at times.  Of course, to look at things more optimistically, your friend might be able to give you pointers if you compare notes. (Tread lightly, of course.)
  4. Examine your reasons for wanting to date this guy.  Is it because he might be hurting and you have rescue fantasies?  Do you strive to be like your friend so much that you want to date the men she has dated?  Just make sure your reasons are healthy and sound.


 Jonathan Alpert is a Manhattan psychotherapist and author.  He appears on national TV commenting on sex and relationship issues as well as lifestyle, mental health, and hot-button issues. Get more of Jonathan’s great advice in his new book, Be Fearless: Change Your Life in 28 Days. And you can follow Jonathan on Twitter at @JonathanAlpert and on Facebook at, and visit his website at