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Dear D'annie: Should I date him or let my Best Friend just sleep with him?

February 10, 2016


Dear D’annie

My best friend and I recently went out for some drinks, and this guy at the bar instantly showed his interest – in both of us! We talked and laughed until the sun came up and the bar closed, and we kept walking and talking until we went home. My best friend is the “one-night-stand”-type, and I am the “long-term-relationship”-type. We both fell for him, and he seemed equally interested in both of us. There was nothing “douche-y” about him, and he seemed like a relationship-type, like me. My best friend claims she only wants to sleep with him, and is willing to back down if I am really into him. The problem is that I have never seen her look at someone like that before. I am afraid that it is going to ruin our friendship if I pursue him, but I really believe he could be the one. I have never felt like this before, and I think my best friend feels the same way! He is so perfect, it feels like a complete waste to just leave it and never contact him again. What do I do?


Dear Relationship type,

I know I’m stating the obvious but you are between a rock and a hard place and that is never easy.  On one hand you feel something for this guy but on the other hand you suspect your friend may feel the same way about his guy.  I am not clear about the interaction times between you, your best friend and the guy other than the initial meeting you mentioned.  However the fact that your best friend is your best friend speaks more to the most important of the two.  While the guy may be the relationship type, friendships have a way of outlasting relationships so before you look at the choice look at the friendship. 


You mentioned you never saw her look at someone like that before; while your assumptions could be correct its a possibility that you saw something else.  Perhaps she has never wanted to conquer someone that much before which you could be reading as her wanting a relationship.  Past behavior is a predictor of future behavior so your interpretation of her feelings may not be the same as her reality of her feelings.  You said “she claims she only wants to sleep with him” which implies that you may not believe her. You also stated that  "she says she can back off if I like him” but you also said that she looks at him giddy eyed.  


I wish I could say it won’t ruin your friendship but I can’t. it could ruin your friendship and here is why.  No matter what happens the other person could end up feeling like they were denied the chance and end up resenting the other person consciously or subconsciously. Additionally once she sleep with him even if she does not have a relationship with him that would limit your future possibilities with him and if you have a relationship with then she won’t be able to have sex with him, its a choice but like so many other tough choices we face the choice simply has to be that which you can live with. Best of luck


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