Waylon finds himself a target when a girl named Meredith decides to use him to make her boyfriend Jimmy jealous. Doesn't Meredith look a little familiar? (she was only in one brief scene on the show... Her real name was never mentioned.)
Waylon's hair is always different everytime you see him in a flashback and I'm not entirely sure of the year this would be since the Simpsons seem to be on a constantly moving timeline, so I based everything on the mid to late 70's... though by now Waylon's highschool years would probably be the 80's... xD Doesn't really matter I guess.
(and yes...Meredith does look familiar...)
You are perceptive! There are so many minor characters in the show, it's hard to keep up with them sometimes!