Shy guy, how to tell where I stand with him?

I've known this boy since elementary school and we 'went out' in 5th grade and it lasted like, a year and a half (I know it wasn't like a serious relationship, so don't reply to this and say something about the whole us being too young thing). But during that time I really became close to his family. His sister (who is 14) and I are best friends still, and his mom is pretty much like my second mom. I have always liked him for he is VERYYY good looking and VERY sweet. The problem is, he is really shy. He has never had a real first kiss, and he is 'scared' of getting too close to a girl. He told all of this to me, and saying things like he is scared to hurt someone or get hurt. I tried to tell him that I don't mind him being shy, and sometimes you have to take chances. I mean, maybe I'm wrong, but he's sending me mixed signals! He told me last week that he wanted to take me out to a movie, just me and him. And then right before we left for the movie yesterday, he invited his friend to go also. Things like that. I just don't know how to tell where I stand with this guy! It also makes it hard because I can see how I could be intimidating because I've had sex and everything inbetween and he knows that.

He's scared you might turn him down, approach him and ask him to go out with you! Hell I'm the same way, if there's a girl I REALLY like I wont approach her, I wait and see how things could go, because most of the girls I date are friends that I don't want to lose. So approach him, ask him to the movies or even to go for a walk or something and talk, sounds like you two would be perfect considering you're good friends, most likely wouldn't have that weird session of awkwardness. I'm sure he'll brighten right up if you ask him, the way I read what you wrote is exactly the way I used to be, too scared to ruin a friendship if the girl doesn't like me, wait for her to ask me.

Hope that helps!