Ray makes a startling discovery when he takes Debra to his 20th high school reunion. It turns out that Debra's "one of them" – the cool people who hated him and used to throw him into the girls' bathroom! Depressed about being unmasked as a "nerd," Ray tries to deal with their mixed marriage.

Debra becomes angry when Ray contributes $1,000, without first consulting her, to his friends' harebrained scheme to open a go-cart business.