i never dated in high school, because it was a stupid contest over who could date who in the popular click. it's useless. actually, that's not true, my first boyfriend was at 14, and he cheated on me. i dated my first real real boyfriend at 19, and it was serious, first love kind of thing, but we were both immature. so maybe date your first person after high school, in college, when sex, and dating is genuinely appropriate. but what do i know about relationships. i've only been in one for 5 years now.