I can't do it!!! I'm such a chicken!!

I know this might be a little too much information for me to be sharing... but I have to get it out of my chest!!
Ok, let me start from the beginning. I am not the easiest girl to approach, this is something that I have realized a long time ago. Men are terrified of me, or maybe they just find me unpleasant or arrogant, I'm not sure, mostly because none of the guys that run the other way has cared to share why they do so.
Anyway, I am usually attracted to older men, always have been. Something about the way they handle themselves, the fact that they know more than I do about life, I don't know, I can't really explain it. However, about 8 months ago I moved to this new neighborhood, very nice place, secluded, peaceful, small. Little did I know when I moved here that I would change my taste in men, well, if you can call him a man! lol
There is this gorgeous guy in his early 20's that lives around the block. And that is where we catch up with what I said at the beginning of this post. I can't seem to get myself to hit on the guy! I don't know what it is. Everytime I try to bring myself to do it, I stop myself. I'm so childish!! If he only knew!
There are a few setbacks that are probably the reason why I can't seem to be able to approach him. He lives with his parents, being so young and all I'm sure they wouldn't like it if an older woman was hitting on their son. You could say, "well, they don't have to know about it", only problem with that is that, like I said before, small, secluded neighborhood. The guy lives around the corner and has family friends a house away from mine. It would be almost impossible for them not to find out. On top of that, he is always surrounded by those people.
I know I'm closing all the doors on this matter. He seems like a really nice guy, he is young (every young man's fantasy is an older woman that is attracted to them).
I don't know what I'm trying to say with all this, and it's not like I'm asking for advice either. I have already gotten all the advice I need, and it comes down to one sentence: "go for it!!"
I just can't seem to be able to do it. Ugghhh! I hate that!
Why can't he make my job a little easier!!