Cameos by actors from Newhart, Taxi, The Bob Newhart Show and Dear John highlight this bizarre episode which opens with a charity auction during which George wins a group-therapy session and Leo wins a van. George reluctantly visits the therapist and ends up working wonders on the group with his straightforward advice. Meanwhile, Leo uses his new van to run a taxi/tour-guide service and picks up a group of tourists who look strangely familiar. His passengers soon realize that Leo doesn't know the island very well and they are being taken for a ride.

George's new housekeeper Margie turns out to have boyfriend problems. He offers advice, and she so appreciates his support that she moves in with him, much to the delight of his nosy neighbors. Unfortunately, the girl's family isn't quite so excited, and George's joy over his young, beautiful and meticulously neat housekeeper is short-lived, after Leo has a miscommunication with the girl's overprotective dad. Meanwhile, Leo, in an effort to help Ted, becomes the restaurant industry's worst food buyer.

Secretive Sheila shows up one day in the bookstore, and George is somewhat stunned when she asks him out on a date. So is Leo, because he can't shake the nagging feeling that he and Sheila have met before. George's date is cut short when Leo finally remembers the shocking truth about Sheila and an old chapter in his life.

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.

Leo has a mild heart attack and, thinking he's going to that big Las Vegas Hilton in the sky, gathers his nine ex-wives together to atone for being such a bad husband. The wives, thinking that Leo is leaving them money, descend on the Vineyard, and on George.

Every week, George loses himself in a poker game with friends. But when Leo finds out that Walt, his supposed best friend, is also part of these weekly sessions, Leo is bitten by the jealousy bug and demands to be included. Meanwhile, Ted agrees to be hypnotized by Ambrose in order to deal with his squeamishness about the delivery room.

While he is reminiscing about Casey's childhood on the eve of her baby shower, Leo remembers that he convinced his old friend Robert Goulet to sing her a song on her seventh birthday. Eager to make a big splash at the shower, Leo tries to get Goulet, who is making a guest appearance at George's bookstore, to sing for Casey again. Unfortunately, this time, the song produces more than just applause.

When the day comes for Leo and Tasha to get married, Tasha has a little trouble with the her memory. As she is saying her vows, Tasha accidentally pledges her troth to George instead of Leo, convincing Leo that she really does have feelings for George. Tasha has to agree, especially when she channels a past life in which she and George were an Egyptian princess and a pharaoh. Now, if they can just divorce in a past life... Meanwhile, Leo invites some of his former mob friends to a bachelor party, and one of the ""made men"" gets a crush on Alice. (Part two of two)

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.