My best friend and I have been best friends for three years, and are as close as possible. Recently, our whole school has started to “ship” us together in a relationship. I actually DO like her more than a friend, and we are both bi, but she always seems slightly disgusted when people mention the ship. Since I’ve been her best friend for three years, I can see that her reaction isn’t real, but she also is expressing a liking for a guy in the grade above us. Any advice on how to ask her out?
LemonVibe 
So, I’m bi and have been ‘shipped’ with a best friend of 2 years before and both of us were ok with it (read: didn’t put up a front), and generally just let people assume whatever they wanted. The only exception was that we had to act a little less friendly when her gf was around- because, yes, unbeknownst to our classmates she DID already have a gf in another school.
This was fine until she and her gf broke up. At that point she was still close to me, but she started putting up a front (acting as if it was stupid/weird/impossible for her and I to be together) in front of others. It bothered me at first but then I realized that the real reason was that she just wanted to get back with her gf and she didn’t want any conflicts; i.e. she didn’t want to invite her gf over for a ‘get-back-together’ moment and have her gf overhear people talking about her being with me OR have me hit on her.
I considered it possible that she WAS a little interested in me and thought that I might return the interest if given a chance. The thing is, she might have been a little interested in me, but was WAY more interested in getting back with her gf. So, she started putting up walls that made it seem like she and I could never be a thing. She made light of our connection because she didn’t want our bond to get in the way of reuniting with the woman she REALLY wanted. She protected her true interest.
It was a little shitty, but I understood it.
SO-what I will tell you is this: Chances are that she is somewhat interested in you, but is more interested in this other guy. Or possibly, she is torn between the 2 of you, and some other issue (like family) makes her think he’s a more acceptable match. You’d be amazed how many gay and bisexual people can openly admit their preferences, but falter or outright avoid dating the very people they’re attracted to when it comes to doing more than talking about it.
My advice is to be a little more open. If she jokes (negatively) about being ‘shipped’, make a joke right back that you’re fine with it-“its way hotter than being with the other b*tches and douchbags around here, right?” If she goes on and on about this other dude, accept that she might be more into him/not ready to date you. But if after joking around she finally stops fronting, go ahead and throw it out there, like, “F’ it- let’s go on a *real date and see what happens.” Tell her that you like being with her and it’s fun, so what could it hurt. If it’s weird, whatever, because at least you’ll have given people at school some shit to talk about, and you’re SO above that anyway, right? 😉