So, I'm talking to this guy and he wants a pic of me. I mean, I have one to send to him and its totally appropriate, like its just me smiling and wearing clothes of course ... is that okay? can I send it to him?
That seems fine to me. But you don't have to send a picture to him if you don't want to. I always wonder why guys would ask for pictures but the last guy who asked me for a picture did because he liked me and he sent me one in return. So it's your decision but you should ask for a picture of him in return.
Depends. People send pictures of themselves all the time online; face book, MySpace, etc. The question is, do you feel comfortable with it? If your having this much insecurity about it right now that should be a red flag right there.