How do I make the first move?

Sorry it didn't work.but hey at least he smiled.
Yes, at this point I would make a first move. Do it someplace busy, just sit next to him in a class or on a bench and start a conversation about anything. That way you can always say you have to go if it doesn't work.

He may just not be ready for any sort of relationship. There are guys like that.

I believe with a simple conversation you both will be aching to have another...
Just remember to be yourself, because if he's shy like it seems, you will be perfect for him and vice versa. I wish you the greatest of courage!

Sincerely,
A Loving Black Man

Steps to getting a guy to ask you out:
1) Be hot
2) You personally don't need any other steps.

Seriously though, even if you're only 1/10th as cute as your picture, most girls would just be mad at a guy for a while for not making the approach (he needs to know that he'll have to do some work to get and keep you).

If however, you're feeling compelled to be generous to this guy, go ahead and break the ice. I once had a girl put a note on my car for a few days (without a signature) just to get the intrigue started. Finally she gave me a lucky break and put her name and number on it. I definitely called, and I was happy to learn that she was in fact the same girl that had been sending me signals all along. We met for lunch and things just took off from there.

But, as the others are saying, since it is 2007 and all you can try the direct approach if you prefer.

Feel free to make the first move, I would be shocked if it bothered him. Most guys really like it when the girl comes up to them, specially if there has been smiling going on. If you talk to him, you could start off with a question about anything really. Take what you know about him and try to bring it up in the conversation.

YES!! THANK YOU A-R Norman!! You have spoken the mind of men! I am a good looking man, with good character, personality, and intellect. But the only problem is that I'm a bit socially apprehensive--shy =P so yea!! if some decent looking girl just, key word* decent...don't have to be hot, walk up to me and starts a conversation or even ASK me out on a date, then IT IS ON! I admire such courage and good intention. A woman like that can't be denied.

Anyhow, I think Pickupman's approach is more appropriate for your case. This guy you like seems to be the shy type. Generally, shy guys are more on the conservative side. So you'll need to take it slow and make your move subtle. And finally, I would NEVER use pick up lines on any occasion because you may come across as superficial, insincere, manipulative, etc. And GL! talk to us if you need further help.

I would suggest something different from what PickUpMan said. Not that his advice is bad, just offering another point of view. Don't be gradual, go bust his balls! It would be easier given that you are shy (would you rather bring up your confidence once, or every struggle every single day?). Say something really smart, witty and humorous: "Do you smile like that to your mom too?" As you might realize, this is an all-or-nothing strategy (isn't love so?), but I think it's worth it.

It would make him think: "Hey, this girl acts all shy but she has a wild side! She drives me crazy..." If all else fails, you can heed A-R-Norman's advice and enjoy the ice cream...

I would go ahead and make the move. Don't go overboard just do so gradually. Here is how: When you pass him smile and say "hi." Do this a few times and then progress to a bit more small talk like "man that assignment was tough" or "did you see what the teacher did to..."--hopefully you get the picture.

This should evoke a response and a conversation from him...from there you should feel more comfortable with longer discussions and you may want to pack a few jokes in for good measure. If he is still a bit shy when it comes to asking you out...ask him what he does for fun or on the weekends...then ask him to meet up with you sometime and have fun.

This may take several weeks or progress quicker depending on how comfortable and/or outgoing each of you is.

Go for it, I'm positive he'll be wanting you!

Best of Luck.

Also--more and more and more men are saying they wish girls would open up more and speak their minds...so go for it!

This is 2007--Make the first move and be prepared to pay fro the date if he says yes. If eh says no, then lick your wounds, eat a pint of Ben and Jerry's and find a new target--this kind of "practice" will give you confidence in the dating area--not everyone will say yes--rejection isn't the end of the world or means you are undesirable--he may have just gotten out of bad relationship--or a divorce--or have family problems he doesn't want to drag someone into.

Go in with a "I can accept whatever", then walk up and say, "Hi, my name is _____, and follow it by an observation like, "Man it has gotten cold/hot lately..." you know, a conversation starter....

I agree with PickUpMan, if you don't want to wait for him to make the first move, then you make it. I don't mean like go up and start randomly talking to him. But if you see him around or next to you say hi, if he replies back cool. Maybe even say "hey how's it going?" if you want more than just a hi. Just start slow and if he's cool with you, then he'll open up more and start up conversations with you. XD