How to Go from “Friends” to More

Friends with benefits...and coffeeDear Em & Lo,

I've known this girl "Ashley" since high school band eight years ago. We instantly hit it off as friends the day we met. I know it's cliche, but I've had a crush on her since our first band practice together. She has stated many a time how I'm her "best friend."

However, this past summer we hooked up when both of us were mostly blacked out. That is, we both remember the initial make-out session but don't remember how we woke up in the same bed. We also have yet to directly talk about that night. In addition, we hold hands in a "more than friend way" whenever we walk somewhere while inebriated.

My questions for you are as follows: What are your thoughts on very good friends trying to become more than friends? What are some signs that one friend might have strong feelings for the other friend and, in your experience(s), is it worth it when two good friends try to date?

Thanks for the help,

Best Friend Wants More

Dear B.F.W.M.,

You had us at "high school band." At least, you had Em, who suffered numerous heartbreaking unrequited crushes in her high school band.

Anyway. Hard as this might be for you to hear - given that you and Ashley only hooked up after blacking out, and only hold hands when you're drunk - you're going to have to approach this sober. In the cold, sober light of day, you're going to have to ask out your friend on a date. The only way to know for sure is to be 100% blunt about it. We recommend actually using the D-word, as in, "Would you like to go on a date with me?" Your question has to be 100% obvious so that her response actually means something. (Meaning, if you ask her out to the movies and she says yes, that doesn't count, because she might think of it as a friend-date.)

If she says yes - bingo! It's true love, Hollywood-chick-flick-style all the way. And if she says no - actually, hopefully she'll be a bit kinder and will use the excuse of long-distance - then you have your answer and you can move on and find true love, drunken hook-ups, and romantic hand-holding opportunities with someone else.

Seriously, it's that simple. (And that freakin' terrifying. Sorry.)


Em & Lo