Well, if Lizard Dude can kiss a girl, then I bet I could! Wearing glasses is like the same amount of uncoolness as lacking a personality!
Hahahaha! For some reason I found that pretty funny. As for myself... wellp, I'm 36 years old and never kissed no one but my good ol' dog, Bubba. It don't matter none. No big deal.
Actually, I'm not 35 and don't have a dog named Bubba. XD But I really haven't kissed a girl before (unless you count the number of times that Princess Toadstool has kissed me after I rescued her). But I do have a picture of a girl kissing me while we sat on a couch. :) We were both really young but it was still cute.
I wish I had some good advice to give, but my own convictions have dried up any experience I could tell you about. My goal is to try and wait to kiss a girl as long as I can, possibly until marriage. I'm sure this sounds rediculous and old-fashioned (and it even sounds that way to me!) but I want to make it special for my wife. (Plus, I don't have any nerve to even think of doing that during a date! XD) I think that if someone of the opposite sex kissed me and then later we broke up and they got a new date, I would feel even worse about that. I don't know how all girls would take that though. I feel a poll coming soon. >_>
But as for you... I think I would let the girl make the first move just to be safe. Then you can have more of an excuse to kiss her! However, if both of you wait for each other or don't want to then... uh... it's up to you I guess. It's not the end of the world if you choose the wrong time but it could be a little embarrassing.
So, in summary, I hope that my something came out of my random rambling. Maybe the internet has some good advice. Good luck whatever happens!