Search Results: good sense of humor

There is this one girl who kinda has the whole package. She is funny, has a great sense of humor, nice, pretty, has nice hair, and really, good teeth. She dresses well, and always looks clean and put together. Hell she is even a huge nerd from what I hear. She likes video games, and comic books, and goes to comic con every year. But she is on the hevier side. Not overwhelmingly large, but she has bigger hips, and a sort of chubbier face. Is an overweight girl a turn off or should it not matter?

Ok so im 14 and on a scale of 1/10 im a 5 or a 6 at max (appearance wise). So yea im not the most handsome guy you'll ever see but Im not disturbingly ugly by any means. I have a lot of friends and I would say 80% of the people who know me, like me as a person. Im quite confident and relaxed around girls and something I pride myself about is my sense of humor. I can make basically everyone laugh (girls included) without like humiliating myself or something. Just plain old humor. However, I'm not that "successful" with girls my age. I have had 2 girlfriends before with who out relationships were like 1-2 months long. I'll stop bubbling now. For the past year or so I have been talking to a really hot girl my age but almost only through texts. She has been throwing hints here and there but nothing major that I could REALLY say "oh she likes me". The problem is that she's really stupid and doesn't have an exciting character so during this time that we were talking I wasn't so into her. However, for a while now (1 month or so) I'm thinking of her very often and I really like her (yes suddenly). We will both be at the same Island for holidays in a few days and we have told each other to meet up there if possible. The problem is that even though I believe I have a good chance with her I can't get off my mind that "dude. She's out of your league" thing. Is it really true? Or do I have a chance? Should I go for it? And if yes, how should I approach her?
If you have read this whole thing thank you so much! Sorry if I have some mistakes here and there I'm from Greece... Anyway I would be SO happy if someone can answer me this question :) thank you again for reading all this thing and I hope you answer me!