Dating, friendship

Playing with Fire…..Dating a Friend’s Ex

Dear T,

Please don’t judge me, but I think I have a thing for my best friend’s ex.  My best friend and this guy broke up nearly 3 years ago, and I hadn’t seen the ex until about 2 months ago.  That’s when the guy started working in my office. Since then, we naturally started talking and have even become cool. And my best friend knows this. What he doesn’t know, is that his ex has started flirting with me heavy. And if I’m honest, I like it because I like him.  But, my mind keeps telling me that I can’t go there for the sake of my friendship. However, I’m tired of denying my feelings for this guy. Plus, my friend has moved on and has a good man. What do you think I should do?


Playing with Fire

Dear Playing with Fire,

You’re alias is quite accurate, because you are indeed potentially playing with fire.  Attempting to get involved with an ex of your bestie, is a dangerous game I usually caution people against. There are three reasons I am typically not in support of playing it.  One, there is a good chance the bestie won’t understand why there are millions of men in this country and yet you happened to develop a thing for a guy he used to be in a relationship with three years ago.  Even if he is happy in his current relationship, your bestie will more than likely feel some type of way about you picking up his “left overs.”

Two, if you and this ex wound up getting into a relationship, that means at some point your bestie will be around you two.  And I’m willing to bet, that situation is going to be awkward for you, the ex, and the friend.  Let’s focus on you for a moment.  What happens when your buddy and the could be new boo start rehashing memories from the past?  Are you sure you won’t get jealous?  Then to think about your friend having had sex with your new boo.  That would drive many crazy.

And last but not least, I don’t advise dating a friend’s ex because I question the motives of the ex.  Sometimes a former love will attempt to get involved with an old boo’s friend, just to get under the old boo’s skin.  Since it’s been three years that your bestie stop talking to this man, I don’t think this is the case.  But you never know.  It’s definitely worth you thinking about it.

Now not to confuse you, but I can actually envision a situation in which it may be okay to date your bestie’s former flame.  If the attraction between you and the ex is so strong?  If you know in your heart of hearts he could possibly be the one?  And if you are willing to possibly lose a friendship?  Then go ahead and see where this thing with ex goes.  But make sure you talk to your bestie about it first though in an effort to preserve the friendship.

Suggestions going forward.

  1. Put some distance between you and this man, and try talking to other guys. You may find your feelings for him go away.  If they do, then you saved yourself an uncomfortable predicament with your friend.
  1. Also, think about if the roles were reversed. Would you be upset if you found out your bestie tried to date one of your ex-boyfriends?  The fact that you wrote to me signals you would feel some type of way.
  1. Again, if the attraction between you and this guy is just too undeniable, and you know in your heart it’s worth pursuing, talk to your friend about it first. You don’t want someone else to tell him about you and ex before you have that conversation.

As always nothing but love,


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