Season 5

Doug's father starts showing his age.

A pre-Christmas argument with Willie nearly gives Doug a heart attack; Buddy invites her school's janitor to her house, where he quickly endears himself to everyone but Kate.

Buddy and Nancy find themselves in a love triangle; Annie dabbles in the occult.

Kate finds out she's pregnant; a friend of Buddy's, on vacation from her all-girls school, picks Willie as a seduction target.

Two friends of Buddy's who have been going steady for 3 years are having relationship problems -- and when she tries to help, the results aren't quite what she expected; Nancy is having trouble at work, which starts to affect even Timmy.

Buddy's friendship with a teacher gives rise to rumors; Annie uses questionable tactics to get Willie to let her interview him for her school paper.

Willie finds the director of his play more interesting than Rachel; Buddy insists on buying an old sports car, over Doug's objections.

Buddy has an ambiguous relationship with a nerdy schoolmate whom Kate is training for a piano recital; Nancy begs Annie to teach her how to roller-skate, so she can go to a party with a handsome fellow lawyer.

A schoolboy has a crush on Kate; Jeff, now an in-over-his-head rock manager, blows into town with his band.

Elaine resurfaces in Kate's life after being dumped by Fred for a younger woman. Meanwhile, Annie experiences abandonment issues, too.

Buddy tries to make everyone think she didn't get into any of the schools she applied to; Doug wants Annie to share his obsession with baseball.

Annie gets picked on by her classmates, for being too smart; Buddy, studying for her SATs, worries that she's not smart enough.

Doug is upset when Buddy starts dating a 21-year-old; Annie is jealous of an old friend who has matured much faster than she has.