Dear Mistress Maeve,
When a good friend of mine moved out of town recently, she left behind a great guy. They had only just begun dating when she had to move suddenly, and I guess they ended it, because I haven't heard her talk about him since.
I ran into the guy the other night at a show, and we flirted and chatted off and on all night. I was overcome by a sense of guilt toward the end of the night, so I left without saying goodbye. I'm not sure where my friend left things with him, and I don't want to upset her. He just sent me a friend request on Facebook, and I'm not sure what to do. He's cute and nice, and I am totally attracted to him, but what do I do about my friend who now lives five states away?
Dating a friend's ex is a difficult situation that requires extreme care, even if they only dated for a little while and she now lives five states away. First, determine whether or not there's potential for a real relationship with this guy. Thus far, you only flirted at a show, and you do not want to mess up your friendship over a would-be hookup.
If you genuinely want to pursue something with this guy, talk with your friend (preferably before she sees that you've become buddies on Facebook). Let her know something may be on the horizon with her ex, but that her friendship is also valuable to you. Remember, you're not asking her for permission to date him, but you are trying to show her respect by filling her in before anything happens.
Last, be ready for your friendship to change. No matter how thoughtful you are during this process, your friend will most likely feel uncomfortable and may pull away. In this case, it's not her physical distance from her ex but her emotional distance that will determine the outcome for your friendship.