Actually, I just mentioned someone like this in my signature, but it really upset another moderator so I took it out.
When I was in 8th grade, I had the biggest crush on this guy named Kevin. He was in 9th grade and he was sooooo cute; and such a bad boy. And I was this prissy, preppy little thing so I guess I thought he was Pittsburgh's version of James Dean in "Rebel without a Cause"! lol
Ninth grade comes, Kevin is in my study hall. Turns out he was still in 9th grade! Still cute. Still a badboy. Still crushing on him.
Tenth grade, I'm finally allowed to date. Dates with Kevin were usually comprised of me taking my school books to the basketball courts in Kevin's town (where the bad boys hung out! Bad boys in 1984 weren't quite as bad as bad boys in 2004) and studying while he and his cohorts played ball then he'd take me out and buy me a hamburger and shake with the money he won

He is still in ninth grade, by the way.
Eleventh grade rolls along. For me, at least. Kevin is still toiling in ninth grade. When he shows up. I'm finally figuring out that he might not be the guy for me.
Twelfth grade. Kevin is MIA. I hear rumors that he's in Shuman Center, where bad boys go when they're too bad.
Never heard from him again, unless you count the times his name popped up in the "Crime Log" section of our local paper. My mom would always be kind enough to clip it and send it on to me

Last time, I believe, it was some kind of drug related thing. I can't remember details, but it was something big. I guess he's someone's prison b--ch now. Sigh.