Sasha Answers: Should I Make Moves On My Friend?

April 30, 2012 16:38:24 Posted at April 30, 2012 16:38:24
Sasha Posted by Sasha

Hi Sasha, I need your advice.  I’m 25 years old and I’ve been friends with this really great guy for 13 years now, since we were in the eighth grade.  I knew then that he was into me (maybe more than that) for many of those years, and he later confessed to this years after high school.  Anyway, despite him feeling this way, he never did anything ballsy or confess to it until after the fact.  Or maybe I was just good at playing dumb.  Regardless, he was one of my best friends in growing up.  He grew up into a good looking guy, popular, freakishly smart, with a smart-ass sense of humor and annoyingly witty...and there was still nothing there for me, even though he had so much going for him then.  I feel he eventually got over me around our senior year, when he became serious in a relationship, one he is still in to this day.     
Recently, we kind of started talking again and this time, it feels so different for me and I’m starting to wonder what it would be like to “be” with him.  After years of dating a wrong guy for a long ass time, I finally see the qualities I want in someone and I realize now that he has had them all along.  And about his GF, when I asked him why they’re not married yet, he says things like, “I know she wants to, but I’m just not sure yet that she’s the one.” After 7+ years, he still doesn’t know?  And another thing, I’m also scared to hurt her because she’s always been a little suspicious of our relationship despite it being totally platonic. Then again, I’m not entirely sure if he’s happy or unhappy with her and I don’t want to be selfish and just ambush him like this.  I’m so confused.  Should I even tell him or keep this all to myself and hope it passes?!  Please tell me what you think.  Thanks! A

I think before you do or say anything you need to give this some more thought. You REALLY need to ask yourself why all of a sudden you have these feelings for him, because from what you wrote he hadn’t really crossed your mind until you guys started chatting again.  And to me, this sounds pretty fishy….

So A, is this really a case of buried feelings coming through or are you just tired of being lonely?  Have you been beaten down by a string of bad guys so much that you’re just looking for someone “safe”? Can you see yourself marrying him?  And more importantly can see yourself f-cking him?  The latter is crucial because while he might be perfect on paper, if you’re not sexually attracted to him things will go soft….quick.  

You need to be solid with these answers because if you’re about to do what I think you’re going to do, you need to be aware of what you’re walking into.  You’re not only putting your own heart at risk, but you’re going to f-ck with two other ones while you’re at it.

No matter how you slice it this situation is one big shadefest. But if you truly love this guy and you feel like he’s “the one”, then I’d get in, lay it out there, and then get the f-ck out.  Now, if he says no, or not yet, or he’s confused - let it die.  Do not make any more attempts. Wish him well and move the hell on.  

A, if I’m being really honest here, it seems like you’re just teetering around with this idea and in my opinion that doesn’t warrant any kind of action on your part.  It’s not worth the potential emotional carnage.  I think it’s in everyone’s best interest for you to back off from this situation all together until you’ve really sorted out where all these feelings are actually coming from.

Keep me posted! Thanks for the letter and keep sending all your style and advice questions to

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