Go for it. You are beautiful and you come across as a good and decent person. What can anyone ever accuse you of being except "yourself"?

Think of it differently. By being yourself and assertive, you are forcing him to react and respond. You'll have a pretty good idea of who this guy is by the way he reacts to you. You have nothing to lose and everything to gain because if you try and set up a situation where you are calculating his response to fit what you would like him to say and do, well, you are only setting yourself up because in the end, he will be himself. You might as well see straight away how he reacts to a beautiful and confident woman. Let me phrase that differently, you owe it to yourself. Go for what you you want. If he doesn't react the way you would have hoped, well, maybe he'll come around again some other time, but if he doesn't, you may have saved yourself a few years of frustrations. I have read so many blogs on this site of wonderful girls who wanted to give a guy a chance and they tried to make things work. Bottom line, go for it. He'll sink or swim. And if he sinks, he won't be dragging you down with him. I think your mother is right on this one.

Wow. Annika summed it up in a dozen words.

I find it flattering to be asked out. Worse case is he says no and then you can move on. That 's easy. Best case is he says yes, then the hard part begins. Good luck and just be yourself.

Correction: The wind cries cake

I think your instinct to suggest hanging out in a casual way, subtly indicating interest and letting him take it from there, is a good one. It provides him with enough of a green light to take a risk if he's shy, while still letting him take on the traditional guy role of instigator/pursuer in taking it to another level. I also once had a girl I had a casual friendship with tell me she had a romantic dream about me, which I took as an opening. We ended up living together for two years.

Annika is right. Since he likes chatting with you, he's probably comfortable with you. It's safe to say he probably thinks you're hot. This is the 21st century, so you can safely disregard your mom's opinion.
Your idea of asking him if he wants to hang out is probably the right way to go - something casual, without a lot of pressure. He might even take the hint!
You may or may not be right for each other, but the only way to find out is to try.

Go for it.. Ask him to do something in a casual setting...

Go get him!
Seriously. If he's comfortable around you. Go for it sweetie.
Have fun!

there is no perfect moment. or at least i've never seen one. you just gotta do it.

I'd go for it too, invite him over for a beer and football, then kind of ease your way over there and tell him you feel comfortable in his arms. I'd fall in love if a girl did that to me, oh wait the fiancee did

I really like it when a girl makes it more obvious that she is interested. Even better when they make the first move.

http://imgs.xkcd.com/comics/friends.png

somehow, if he says no, we have to say work into the conversation that famous " let them eat cake" quote.

You're a woman. A beautiful woman at that. That gives you a very distinct advantage over man. That advantage being subtlety. You could drop a hint or two, like, you know I'd really like to see "insert movie, band, thing he might be interested in". Just find out things he likes and when one of them interests you, you could point him in the direction of asking you. If those don't work, and being a man I can say with an 85% certainty they won't, just smack him in the head with a 2x4 and drag him to dinner.

If it was me, on the other hand, hell just ask I like women that speak their mind and treat me like an equal.

go for it, always go for it, even if it's just so you cant kick yourself later cause you didn't.