Fail-chan, I think you just need to build a bit of confidence.

Are you in high school? College? Either place is a good place to start. Perhaps a more casual relationship or dating experience to start with might be better.

Don't go looking for love. It doesn't happen like that. Not often, at least. Instead, find an available-looking guy that's a bit substandard for your tastes who might share something in common with you. Maybe someone you've talked to once or twice.

You'll feel less intimidated this way. Suggest to go have coffee, or study together. Out of the blue, just like that. Don't pile on pressure. Don't go ZOMG IM SO LONELY. It doesn't matter if you stumble midway through talking, either, or anything embarrassing like that. You're just trying to get some attention from this guy. If he's interested at all, he'll pick up and take over from there. After all, a lot of us guys are really shy too, and wish that we had opportunities like that. Some of us are really afraid to meet women.

Don't get discouraged if you get turned down or brushed off. Just keep up hope. Try again after a little while. This is a great way to make friends, as they can introduce you to other people, and if you end up really liking the guy, and he's giving off the same kinds of signals, you might have something there.

Of course, this is just my advice. I've never dated a girl, never had a girlfriend, never been kissed. So take it with a grain of salt.