You don't sound like you are comfortable in your own skin. Magazines, movies, and T.V make us jealous and we want to look like them. Sweetie, thats all smoke and mirrors. Trust me when I say they are human and underneath those fancy clothes and what the make-up and hair artists, they are just as messed up as we are. (if not more so. )
If this man is right for you, big boobs are not necessary. A perfect body is not necessary or even a pretty face. (I bet your beautiful) What really is the sweet spot is what is inside of you. Your personality. If you are beautiful in the inside then your beauty will flow out.
You know he might feel the same way as you. Invite him over for dinner and a movie. Just the two of you. See if you can get the ball rolling. He knows you if you are friends (right?) That is the best way to be in a relationships. Friends first then dating. He might be scared to approach you in fear you might turn him down. Make the first move! I know you have an inner diva.
Keep us posted.