So, I know this topic has come up many, many times, but I have always found the advice (including my own) inadequate and therefore in my insanity I will try again, because even though it hasn't worked before there is a possibility it might now. HOW??? I think about this, and realistically, I don't think it is possible to ask someone out without knowing for sure that they are bisexual or gay already without alienating them completely. Example: I theorectically ask out someone I am now loosely friends with, let's call him Cole. Cole is great, and he has never to my knowledge indicated any form of homophobia, not is he dating anyone. But on top of the fact it's already awkward to ask someone out, he could possibly either: A) misinterpret it as going out as friends B) actually be freaked out that a guy asked him out and be uncomfortable around me forever Granted it would be out of character for me to ask him to go on a friendly outing, but people mistake lots of things for other things because they are oblivious to other people's emotions. I think it is almost just as awkward to have it be misinterpreted as to actually say "like, you know, on a date..." After asking someone to go somewhere with you. I guess the only two solutions I can really postulate are to directly ask someone if they are interested unambigously with the idea of going out with you a date (which is essentially the first most normal scenario and also terrifying because when do you even do that), bring up the topic when out with the person on an excursion that you ask them to attend with you (at which point I would be terrified he would freak out and leave ruining the entire experience...), or ask them their sexual orientation and then if they respond positively proceed as planned (also awkward and terrifying). Honestly, I'm not of the opinion that anyone can even have some miracle way of asking someone out... it will ultimately be awkward and probably publicly humiliating if someone turns you down because it's probable they will tell people and you will forever have a void between you... So does anyone have some real advice on how you overcome the barrier of fear, not of the rejection itself, but of the awkwardness that follows, the rumors that will rush around school, etc? It will just make things a lot harder if it becomes awkward to talk to a large group of my friends simply because I asked one of them out and they said no... Additionally, how am I supposed to flirt with a guy, in a way that is technically acceptable so that they don't feel wronged if they are straight... I don't think it is fair to have to not try and hit on people just because I am attracted to the less common gender. And I'm sure I have said, with my formerly unwavering conviction, that you have to just learn to do it regardless, but now that it is possible it has become infinitely more daunting of a prospect.