Air date: 10/24/00
Mary's wealthy sister Renata Albright has donated a large sum of money to have an extension built onto Pendelton University, but Mary knows that it is in fact a spiteful gesture designed to quite literally block the sunlight into her office. To retaliate, Dick schemes with Mary that he will woo Renata, win her, and then break her heart. Meanwhile, Sally and Harry are given ten thousand dollars by Renata to convert their house into a teen center.
Fear and Loathing in Rutherford
Air date: 10/31/00
Tommy is still reeling from his breakup with Alissa, but Sally and Harry convince him that if he can find an excuse to go over to her house, he can persuade her to watch a movie with him. When the pair leave the house together, however, Strudwick is suspicious and confronts Dick. Mrs. Dubcek suggests that they could have eloped, so Dick and Strudwick rush off to track them down before there's a baby on the scene, managing to accidentally abandon Mary in the process. Meanwhile, Tommy has rented a scary movie to watch with Alissa, in the hope that it might bring her into his arms, but Sally and Harry decide to show up and make it more real.
Air date: 11/14/00
Dick and Mary decide to go on a double date with Sally and Don, but things start to become uncomfortable when Dick and Sally begin talking incessantly about how good their other half is in bed. The next day Dick and Sally come to realize that neither Mary or Don said anything about how good they are, and immediately worry that they aren't. Meanwhile, in a food store, Mary and Don run into each other and, consumed by what they'd heard about each other in bed, share a kiss. Elsewhere, Harry and Tommy follow in the footsteps of Jack Kerouac and take to the open road.
Dick'll Take Manhattan - Part 1
Air date: 11/21/00
The Solomons visit a parallel universe, in which they are living in New York City, where Dick is a highly regarded attorney, Sally writes a sex column and Harry is President of NBC, whilst Tommy is a star on Saturday Night Live. Despite this, Dick is unhappy because he cannot find Mary; however, upon entering a basement bar he discovers her, a failed actress-turned torch singer who has renamed herself Kiki Lyle. Meanwhile, Sally discovers that Don is the Mayor of New York, and that she isn't his girlfriend, but his mistress.
Dick'll Take Manhattan - Part 2
Air date: 11/28/00
Dick takes Mary up to his penthouse and wines and dines her, but she tells him that she doesn't believe in true love anymore, no matter how hard he might try to persuade her otherwise. Meanwhile, Sally isn't happy being second fiddle to Don's wife so she asks him to break up with her. Don, however, wants to run for president and so refuses, so Sally breaks up with him; whilst at NBC, Tommy's huge ego and demand for a high pay on Saturday Night Live leads Harry to fire him.