Background info: I'm 18, 6'2", pretty overweight at 350 lbs (Understatement? Heh), and reasonably attractive (excluding the weight, I'd say).

I have two different situations that both have me a little flustered. First off, I'm not shy at all when meeting new guys to hang out with, and I'm okay with girls when the situation is organic (Lab partners, hanging out with a mutual friend etc.) but I have the common problem of being terribly nervous when trying to introduce myself to a girl that I find attractive, but has no clue that I exist.

My first problem is with a girl that I've been friends with for about 8 months now. She's a year younger than me, and says she has a boyfriend that I would get along great with (Although we've never met). I like her quite a bit and I have a feeling that she likes me too. We have a lot of common interests and hang out often. I don't know if I should take a shot, risk getting turned down because she would rather say with her boyfriend, and then make our friendship awkward from there on out, or if I should just enjoy the friendship we have.

The second situation is a girl that I have a ton of mutual friends with, and that I find VERY attractive, but I have never actually met her myself (No organic situations). There isn't any time during the day where I have more than a few seconds to get her attention, so the only thing I can think of is to introduce myself and hopefully get her interested enough to ask her on a date. I guess the only real risk in this situation is getting shot down and embarrassed in front of all of my friends (I blush VERY easily).

I really don't know what I should do with either of these girls, and I also need to work on my own fear of rejection/embarrassment, but the thought of not having tried just drives me crazy.