So there’s this guy who I know and basically I’m not sure if he likes me or not but I like him and I’m not sure if he doesn’t want to be closer to me because he’s been hurt in the past or whether he is just stringing me along. And we’ve known eachother for a while and I don’t know if I’m in the friendzone or not, and I don’t know how to ask him if he wants to hang out without sounding like I’m being desperate?. He’s a sweet guy but I just also ask him where I stand without being awkward. And I find it hard to say how I feel even in the simplest ways because I’m not the expressive type.
I think you said it pretty well, actually. "Hey, I really enjoy hanging out with you and I'd like to hang out some more, but I'm not sure where we stand." If you never ask, you're never going to get an answer of any kind.