My boyfriend says "For guys like me, it can be a turn on to have someone dominant enough to ask me out. I'm a big guy, I'm intimidating. I am an a*****e. If a girl has the balls to ask ME out, then she might just be able to put up with my s**t."
I was the one who asked my current boyfriend out (we've been dating for three years). I asked him on the first date and was the first to admit that I wanted to be more than friends after that first date.
I'd say go for it. My boyfriend always said that he was pleasantly surprised that I took the initiative.
If he gets turned off by that, he's probably not the right guy for you anyway.
But I'm cool with whomever asks first. Like is like and I've never really bothered with much except "positive emotions are good things", I guess. I think everyone can have a chance to express themselves and "like", because I like "like", and I like liking people too. That said, never weirded out! Always flattered. whee