Sam has just obtained her driver's license, and is hoping to get a new car. Despite Tony's tight budget, he manages to buy her one: a massive, yellow eyesore with many safety lights on all sides. Sam hates it, but can't bring herself to tell Tony.
Tony takes a speech class with a very tough instructor, who makes Tony realize that his normal way of speaking is wrong in many ways. After adopting proper diction, Tony soon begins to realize that the course has changed more than just his vocabulary.
Hoping to join a fraternity at his college, Tony and Angela attend a party. While Tony makes a good impression, Angela gets drunk and makes quite a scene. The bedlam lands the two in jail and makes the dean threaten to revoke the fraternity's charter.
Tony reminisces about how he was responsible for his grandfather never being naturalized as a U.S. citizen. He visits a judge, hoping to change things.
Angela hires a new Creative Director and they enjoy spending a lot of time working together. Tony begins to suspect that there is more going on between them than work.
Mona and Sam both get dumped by their boyfriends and they are both in bad moods. The two go out for a night together to help each other cope. Angela takes offense when Tony fears that Mona's idea of a good time may not be ideal for Sam.
Bonnie wants Sam to join her for a weekend at a cabin in Vermont, but Tony forbids Sam to go when he learns there will be no adult supervision. Sam sneaks out and goes anyway. This episode is told through flashbacks of previous episodes that depict other disagreements between Tony and Samantha.
Mona's sister-in-law, whom Mona hated and vice-versa, has died, and will not be allowed to enter Heaven's gate unless she gets Mona and Mona's brother Archie to make amends. Tony is the chosen one to help reunite them, so the Bowers and Micellis make the trip to visit him on Christmas Eve.
Mason has been assigned to teach a history class at Tony's college, and Tony is in the class. Although Mason is nervous at first, Tony's advice helps him loosen up a bit. But while he teaches, he begins ignoring all students except Tony, who is soon deemed "teacher's pet".
Mrs. Rossini introduces her uncle Al, a student of hairstyling, to the family. (He is actually young enough to be her son.) He and Sam are attracted to each other. Although Tony tries to hide his fear that Al will be a bad influence on Sam, it becomes obvious. Mrs. Rossini calls Tony a hypocrite, since Al is almost a reflection of what Tony was like at that age.
Jonathan is running for class treasurer. Hoping to sway some of his classmates, he invites them to his house for brownies and "to meet Sam". While they are visiting, Mona shows everyone the risque magazine cover she has posed for. Jonathan blames Mona for the abuse he endures the next day at school.
Angela and Tony go into business at a craft fair selling tie-dyed T-shirts. Differences of sales techniques soon have them splitting their merchandise and competing against each other.
Tony brings Angela when he is invited to St. Louis to play in a reunion game with the Cardinals. While there, he runs into an attractive woman he used to know when he was on the team. Not wanting to become involved with her, he tells her that Angela is his wife. Angela is willing to play along until Tony and the woman end up kissing.
Sam accompanies Tony on a ski trip. Tony spends most of his time with an attractive ski instructor, and Sam begins to feel ignored. Meanwhile, at home, Angela and Mona suffer from a bad case of the flu, leaving Jonathan to be man of the house.
Discouraged that Angela had to pay for an escort for a dinner event, Mona convinces Tony to ask her out on a date. The date hardly seems like a first for them, though, as they discover how much they know about each other. Things get ugly when Angela learns the reason behind the evening, and attacks an obnoxious comedian.
Angela gets invited to a dinner at which Frank Sinatra is to perform; Tony, a huge Sinatra fan, is to be her guest. When business affairs leave her unable to go, Mona goes in her place, but doesn't tell Tony that the ticket is nontransferable.
Peer pressure gets Sam drinking at a party, and she comes home sick. Tony is furious at her irresponsibility, but is unable to set a good example when his own buddies come over to watch a football game and drink beer. Sam wonders why it's okay for him to drink liquor with his pals, but to punish her for doing likewise.
Angela and Tony's new neighbors seem friendly at first, but soon prove to be irritatingly nitpicky. Arguments ensue, but that doesn’t stop the attraction between Jonathan and their daughter, Heather. The children are forbidden to see each other, but end up being mediators in the neighbor dispute.
As a school project, Sam visits a modeling school run by Angela's friend. While there, she meets Charlie, a friend of hers from the old neighborhood, who is living there. Charlie is unhappy with her life there, and is considering running away.
Angela hires a shy contractor to put a skylight in the kitchen. He takes an immediate liking to Mona, who agrees to go out with him. When he learns that he is not the only man in Mona's life, he abandons the skylight job. Tony accuses Mona of having no respect for men's feelings.
Tony devises a project for Sam’s class is to participate in a Career Week. Bonnie becomes Angela's assistant at the Bower Agency, and Sam becomes Tony's assistant around the house. Bonnie has a great day, but Sam is miserable at her job, and convinces Bonnie to switch jobs with her on the second day. Sam's plan backfires when her day with Angela is no better.
Angela signs Tony up as a country club member, where he immediately finds a new golf partner, Lowell. The man turns out to be an account executive, with whom Angela has been hoping to work. Mona convinces Tony to ask Lowell if he will work with Angela. Tony skeptically does, and Lowell accepts, but then claims that since he doesn't like to mix his business with his personal life, he can no longer be Tony's partner.
An old boyfriend of Angela's visits and reveals that he and Angela were briefly married many years ago, and that their marriage was not officially terminated. She must sign so that he can marry his fiancée. But Brian's old feelings for Angela are stirred up, and he wants to be with her again.
Sam is struggling with chemistry, while her friend is having difficulty with French. Just before the exam, he gets desperate and talks Sam into giving him the answers. Tony punishes her for doing this, but things get worse when, to thank her for helping him, Sam's friend gives her a crib sheet to use on her chemistry test. She decides not to use it, but still gets caught with it.
Angela surprises Tony on his birthday by buying him a new Jeep. Pride and the history of his old van factor into his inability to accept the gift. Soon he changes his mind, but when he decides to sell his old van, he and Sam have a hard time parting with it.