Should I make a move on him?

Question

So here's the deal. I'm going to this big party and there is going to be drinking. There is this guy that I have had a big crush on for like a year and I'm pretty sure he's gonna be here. One thing, though; actually two. He's my boss and he's like twenty years older than me.

Thing is, he is single as far as I know, he goes to these parties and drinks with people my age all of the time, and he claims he is not gay. We barely know each other, but he has known my sister ofr six years and I think he had a crush on her at one time, but now she's married.

Should I tell him how I feel.... would it be wrong if I expressed a desire to fool around with him at this party? I don't know what to do.

P. S. I'm 19, he's late thirties.

Answer 1

Well, I say go for it and see what he says, how he reacts. You're 19, so you're of age, him being your boss might be the thing that might not let him do anything, because if things go sideways, you can accuse him of sexual harrassment.

Just see what he says, you have to know one way or another.