Beer Your Soul

I've fallen for my new best friend, a woman I met two years ago while we were both going through similar divorces. Sometimes I think the attraction's mutual. She recently started dating but hasn't met anyone she's into. I'm going crazy trying to decide whether to say something and risk losing the coolest friend I've met in decades.

--Obsessing

The line from Cole Porter is "Birds do it, bees do it," not "birds and bees get a committee together to discuss it." Telling her how you feel could be icky and embarrassing if she doesn't share your feelings -- and maybe even if she does. You've heard of "plausible deniability"? If you decide to go for something with her, what you need is plausible drunkability. Have drinks with her, get a little fuzzed, and make a move on her. If she recoils in horror, it was the alcohol talking. If she kisses back or, better yet, is all over you like freezer burn on mysterious leftovers, follow up by asking her on a date. (Emphasize the D-word, reinforcing that your interest is more than friendzonely.) Sure, by making a move, you risk losing a friend. By doing nothing, you risk missing out on a lot more. Life is risk. You can either hide under your bed or opt for managed risk. That doesn't mean managing risk out of existence; it means having a plan for damage control if things go badly. ("Captain Morgan, next time, you behave yourself!")