Ask Andi: I Don’t Know If I Should Hook-Up With My Guy Friend Because My Best Friend Did Once

Dear Andi,

This boy from my hometown who I am friends with has an interview in town and asked to crash on my couch the night before the interview.  This is completely normal because we are close and have known each other for a long time.  We have always been friends, but circumstances have had us talking more than usual.  I just got out of a relationship.  We text everyday and stay up late talking.  He is cute, nice, and awesome.  There is definitely a connection between us, but there is one problem.  He goes to college with my best friend and they have hooked up before.  She doesn’t have feelings for him, it was almost a year ago, and they are friends now, but I feel like doing anything with him wouldn’t be right.  Help please!

Fatal Attraction

Dear Fatal Attraction,

This is a pretty sticky situation but with the right tactics we can tidy it up.  They say friends are forever and boys are whatever.  Yet the same “they” who tell us this also tell us that you can’t control who you are attracted to.  This can present a contradiction, but as always, I prefer not having to choose between the two.  You can honor your friendship without having to restrict your love life if you follow the proper steps.

The first thing you need to do is really consider how much you like this boy.  Could it be that he is the first boy you have spent time talking to after your relationship ended?  Really focus on what it is you feel and how strong those feelings really are.  Only you know yourself well enough to judge excitement from enticement. If you come to the conclusion that it is the thrill of someone new and being single again, then problem solved.  If, however, you are unsure of how you feel, or certain that you have a crush then focus on the next few suggestions.

You need to clear the air with your friend.  Don’t leave her in the dark.  Whether you being with him will hurt her or not, hiding it will find some way to cause tension.  It can be as simple as her being upset because you didn’t update her on your love life, or as difficult as her feeling betrayed and back-stabbed.  If you let her know sooner, then you will not be building a case against yourself.  Plus, you can get an idea, early on, of how she feels about the situation, which is better than after the fact.  

Casually bring up the fact that he is staying at your place before his interview, or, if she knows already, allude to it in one way or another.  Once you are on the topic of him, spontaneously (or at least seeming to be) ask her what ever happened with them.  Ask if it was a one-night-hook-up-with-your-friend type of thing, or if she ever had feelings for him.  Whatever her answer is, you, being her best friend, will be able to tell if there really was a crush on her end by the way she responds.  If you sense she had strong feelings for him, or still has residual feelings, make sure he stays on the couch. I say that because unless you have some undying love for him, a crush is minor but can do damage to your friendship, so find another crush.  If you feel like she didn’t ever like him or if she is over it, then go ahead and tell her you have been texting a lot and it’s causing you to think more about what your relationship with him is.  If you find it hard to be honest with her at this point, then that shows you really think it will hurt your friendship. At that point, it’s up to you to decide what to do about it.  However, if you can tell in in one fashion or another, it will be the best way to see how she will really feel about this beforehand. Therefore, it is important that you ask her again how she feels about him after knowing that you felt a certain way.

I know this is such a sensitive situation and you want to tread lightly.  If you act with good intentions as opposed to being secretive, then your friend shouldn’t get angry with you. She has to understand that your initial intentions of talking to him were to arrange plans for his visit and nothing else.  It is better to figure everything out before so there is no mess left over to clean up.  You can be a good friend to her by getting her blessing and still get your man.  If she doesn’t give you her blessing you at least handled it how a good friend should, and then it is up to you whether or not to carry on without her approval.

Xoxo Andi