I agree with the just biting the bullet and asking him out. Just because he comes across as confident, doesn't mean he actually is all of the time. there are so many factors that could stop him from thinking you are interested in him. Just go for it.
I know that this topic is an old one, so I don't know how much my response now will mean anything, but update us on what has happened since then! I hope everything has ended up well.
