One of Charlie's old partners in crime dies, leaving Charlie to reevaluate his own reckless lifestyle
Evelyn offers to pay for Jake's college education, leaving Alan to wonder if he ever needs to work again.
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.
A new girlfriend wants Charlie to sleep over. Meanwhile, Alan has trouble making a punishment stick to Jake.
Alan tries to get away from Judith. Meanwhile, Charlie and Herb go out on the town.
When Judith kicks Herb out of the house, Alan hopes for reconciliation.
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 lends Charlie money and crosses a line in his attempts to get it back.