Heh, yeah cocky is not cool. I too went to a "nerdy" all guys school. Hell, my prom shirt said "socially awkward" on it as a joke (a well known magazine in Dallas had made a comment about our seniors being socially awkward). However, if you just be yourself then it shouldn't matter what school you go to or what opinion is generally held about your school. If she likes you for who you are it really wont matter