Okay... first off, this guy is a guy I've only kind of thought about dating. He insists he's straight but he just likes to goof off. And I kinda believe that, but there are times when I don't know. It could be, possibly that he's just very open about joking because he and his sister have lesbian parents. But then there is this one time that makes me think he could be at least somewhat serious. There was this one time, during a theatre practise, I was backstage and upset about some shit that had been happening, and he could tell. He asked if I needed a hug, I initially declined, but then came back like 2 minutes later and admitted that I did need one. Little things he does like jokingly lifting me up like I'm some kind of :***:ing princess (but then again anybody can do it, and almost everybody has since I'm only about 100lbs) I know a hug doesn't really mean anything. But, I don't know if it's wishful thinking, or if my gaydar is pinging on him. He does know I'm gay, so... How do I ask without making shit awkward...
Well, you can directly ask him, but I guess that's not the way you prefer. :icon_bigg You could flirt a little with him and see how he responds. When he dismisses it completely, it's likely that he is not interested. But he might flirt back, who knows! I think it's a start. See how it goes. (*hug*) Good luck!
He insists he's straight. Whatever he may be, you can only take his word. You'll only hurt yourself squeezing every action he makes trying to convince yourself he's something else. Drop it. The hug and the signs you mentioned are no big deal, anyone can make them if they feel comfortable enough with their sexuality or that's the kind of person they are.
I don't agree with you entirely. For some, a hug really is a big deal, and since there's no information provided about the personality of the person, you can't conclude it's no big deal. :icon_wink I wouldn't hug any friend currently. Thus me hugging someone would mean there's something more going on.
He knows about you, just ask him... but, do it in another way. Don't admit that you like him, ask him if he likes you. Something like - "hey <name> do you like me?", then he will say yes... then you say "but... really like me, like, like like me?" and then... you'll have your answer. If you are not up for this mushy stuff... simply ask directly if he is interested in you. I would... prepare him beforehand for this, however. Like, be a bit flirtatious (not too obvious) with him, make him miss you (like, don't hang out for some time), be close to him, make him feel comfortable... share intimate stuff... Or... you could just start asking him stuff like "hmm, do you think <somerandomdude> is gay, isn't he hot, maybe i should ask him out". Something like this, you get the idea right? Make him jealous (if he does like you he will very very very quickly become jealous and this will translate into anger towards you. If he starts encouraging you and feels happy for you then... yeah, tough luck. Also... you weigh 100 lbs, how cute is that xD, start munching on some high protein food.