Believe me, I understand the desire to make it casual.. in my dating days, there's no WAY I would have explicitly expressed an interest in a man unless he had done so first. Pathetic, yes, but my fears were that he would be thinking, "Are you KIDDING? Of course I'm not interested in YOU..". And then go laugh about it with his friends or something.
Thanks so much for saying that, you wouldn't believe how much it struck home - that's exactly how I feel!
Honestly, the only reason I'm even considering asking this guy out, is because he made a comment about me a few weeks ago and I sort of did a double-take (an invisible one, hopefully ), and thought 'Oh! I didn't know he thought that about me at all!'. So I kind of got a bit of courage. Then I talked myself back into 'I'm misinterpreting, forget it'.
I'll test out the waters next week, and if it seems right, I'll ask him.
Been there, done that, got many t-shirts with the self esteem issues. It can really cripple you if you let it.
I realized, though.. there were times that guys expressed interest in me, and although I wasn't interested at all, it NEVER made me think badly about the person, or want to make fun of them. It's flattering, even if the person is not your type.
I've missed a lot of things in life because of self esteem issues and social anxiety. I try sometimes to think of what the worst-case scenario will be. For example, maybe I'd be a bit embarrassed. But then I think, it wouldn't be the first time, and I'll recover.. and the possible benefits of taking a risk usually far outweigh whatever the worst-case scenario is.