Charlie finds himself re-examining his wild ways after an old friend dies during a visit.
Alan contemplates retiring when Evelyn states that she'll take care of Jake's college education. Meanwhile, Jake displays a talent that may eliminate the need for college altogether.
Charlie finds himself in an uncomfortable position when Jake takes off with the daughter of a former NFL player. Charlie's Mercedes seems to prove a boon to Alan's love life.
External Link - Click here A new girlfriend wants Charlie to sleep over at her place. Meanwhile, Alan has trouble enforcing Judith's grounding of Jake.
Alan tries to get away from Judith. Meanwhile, Charlie and Herb go out on the town, and Charlie uses the threat of military school to get Jake to do chores.
When Judith kicks Herb out of the house, Alan hopes to reconcile with her.
Discovering Miss Pasternak, Jake's former 5th-grade teacher, turned to stripping after her fling with Charlie, he tries to help her turn her life around.
Alan is sure that things will turn bad when Charlie starts dating his receptionist.
Alan, Jake, and Charlie all decide to try new things: Alan is dating more than one woman, Charlie learns to cook, and Jake experiments with beer.
Alan goes too far in effort to collect $38 he loaned to Charlie. Evelyn arranges a job for Jake