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Buddy Crush

Dear Cary Blackshaw,

So, I’m in love with my best friend.  I know this is a common occurrence among gay friends, so hopefully you have some ready-made advice.  At first, I wasn’t interested in him romantically, but as the years have passed and I’ve realized how amazing he is, I find myself pining away for him.  I don’t have any other close friends, and I love how he makes me feel loved, appreciated, and worthy of his time.  He is the only person in the world with whom I truly feel 100% comfortable just being myself.  Based on some of his actions, I have my suspicions that he may feel the same towards me, or at least has some feelings for me.  I honestly feel we’re perfect for each other, but I’m scared of approaching the issue with him because if he isn’t of the same mindset, I don’t want to lose the best friend I’ve ever had in my life.  We have so much fun together and he means the world to me.  It will sound silly, but I really don’t think I’ll ever find anyone else who makes me feel the way he does.
What should I do?

Sincerely,
In Love With My Best Friend

Hi In Love,

Your situation reminds me of that Whitney Houston/Stevie wonder song “We didn’t know.” If you don’t know it, I highly recommend you look it up; it’s from her I’m your baby tonight album (so pre-crack). But basically it’s about two friends who didn’t realize they loved one another. And based on what you’re telling me, it’s quite possible the feeling’s mutual. However, there is that possibility that he’s completely  oblivious to it all (some people really can’t see what’s staring in front of them), but again, I’m thinking that’s probably not the case.

As the old saying goes, “a drunk man’s words are a sober man’s thoughts” That’s right, get him drunk. Not wasted, just pretty tipsy so the tongue starts spewing things. And do it somewhere fairly public, like at a wine bar or a cozy restaurant. I recommend red wine (my favorite is Port and yes it’s a dessert wine but I don’t care, it’s delicious). Just talk and see where it leads. By having it in a public setting, it means that if something said piques your interest, you won’t be tempted to jump his bones right then and there, and we can’t have that. Just take it slow, but above all, be yourself. Of course that’s a double bind; how can you tell someone to be themselves when the act of being yourself is just that? But we won’t get Zen on this. Just do you.

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