My moral dilemma began two years ago when my good friend H took a large group of her friends on a trip to Hawaii to celebrate her new kick ass post-grad job. This three week vacation included: myself, a mutual friend from university F and H's childhood friend R. R and F hooked up a few times on this trip. F had a man back at home. Once we returned, F confessed to her man and they eventually reconciled with strict instruction that she would never speak to R again. To my knowledge she had R have had no contact since. F moved to another state to live with her man and has remained there for the last two years.

R, H and I all happen to work in the same city so we would occasionally meet up and hang out. The hang outs became more frequent and eventually R and I became close. Nothing physical has ever happened, but it's pretty obvious that this relationship is no longer just platonic. About two weeks ago, the last girl he dated straight up told me that they broke up because of his feelings for me. I confronted him about this and he admitted that he wanted us to pursue a relationship. I told him I couldn't because of his fling with F.  He doesn't understand why I would hold on to "some meaningless hookup" with a girl " I barely talk to anymore". (While F and I have grown apart, she is still my girl and I would never want to hurt her.) So, R essentially gave me this ultimatum: I need to decide what to do about our relationship so we can either "be together" or "move on". 

This is further complicated by the events of last month: F got engaged to her man and I went to visit her to celebrate. After more than a few too many, F confesses that she has never forgotten about R and calls him her "what if guy". I asked her about it the next day and she blew it off. She claimed that she was just freaking out about getting married and we didn't speak of it again. I haven't told R any of this. I am completely torn.  What do I do? M


Here’s my general rule of thumb when it comes to hos before bros:  I will never ever tap a dude that my good friend has had a legitimate relationship with.  Like, if the words “I love you” have been uttered and/or they defined each other as boyfriend/girlfriend at one point they are off limits.  No matter how hot the dude, no matter how big the spark, I have to pack my heart away.

So M, if you operate on the same logic then it’s good news for you, because it means buddy is free game.  Sure, your friend might have liked him back in the day, but the fact is, they were nothing more than recreational f-ck buddies; that’s not enough for her to lay claims on him.  That, and the added fact that she’s moved on and is about to marry (!!!!) someone else.  In my opinion, that clearly null-and-voids any entitlement.  

One caveat though: I do think you need to give her a heads up on what’s going on between you and R.  I wouldn’t say anything just yet, but if things start to get a bit more serious you need to tell her what’s going on - it’s just the stand-up chick thing to do. 

Thanks for writing in and keep your advice questions coming in at [email protected] xx