Leo and George enrol in a baby care class in an attempt to ready themselves for grandfatherhood, but their first assignment leaves them sifting for ways to reverse their troubles when their ""baby"" — a flour sack — has an accident. Leo wants to prove to Casey that she can count on him to babysit, so he enrolls himself in a baby care class, dragging George along as well. The two men are by far the most unusual couple in the class, and their first assignment is to care for a 10 pound sack of flour as though it were their baby. Unfortunately, the ""baby"" accidentally rolls off the roof of Grandpa George's car, and he and Leo then concoct a scheme to get a new ""baby,"" hoping no one will know the difference.

Leo is a steady, two-carton-a-week smoker until George demands that he quit. While trying to get Leo to stop, however, George picks up the habit again, after a 15-year hiatus. Even George's doctor can't convince him to give up. Finally, armed only with their willpower and crossword puzzles, George and Leo decide to hole up and go cold turkey.

George goes to war when a bookstore chain sets up shop on the island, offering 10,000 titles, CD-listening booths and cappuccino, and the owner vows to put George out of business. When Pendragon's, the flashy new bookstore with cappuccino and CDs, opens on Martha's Vineyard, George isn't worried about the competition. That's until Pendragon's manager May informs him that she's planning to run him out of town, which forces him to activate his secret weapon — Leo, and all his boyish charm.

When George begins his new job teaching a business class at the local college, he discovers that his housekeeper, Margie, is one of his students. Then, George's new boss, Dean Shirley Martin, jumps to the conclusion that George and Margie are having an affair and fires him the first day for sexual harassment. George is mortified when Leo, Casey and Ted throw him a surprise party to celebrate his new career. Meanwhile, Alice tries to find a roommate and ends up with a male underwear model.