Air date: 2/25/03
Rory comes home with exciting news to tell Cate: the racecar driver Carter Tibbits has asked Paul to write a book about him. Carter has also invited the Hennessys over to his mansion for dinner. While there, Paul makes a joke to the kids: "$20 to whoever steals the best thing!" Paul seems to make a good impression on Carter, and it looks like Paul will get to write the book. But when they get home, they discover Rory took Paul's joke too far. It turns out that Rory stole a picture of Carter and Paul Newman. Paul sneaks to the mansion and returns the picture. Later, Carter's crew chief Cody Grant arrives at the house and tells Paul that Carter has turned down Paul's services. Paul was caught on a security camera when he was returning the picture, and he goes to Carter to straighten out the situation. While there, Rory confesses to having stolen the picture, and Paul was returning it. Carter sees something in Rory that he looks for in all the students in a program for at-risk kids that he runs: character. Carter asks Rory if there was anything he could get for him. It appears that Rory is going to ask Carter to reconsider having Paul write the book, but he ends up asking for the security camera tape with Paul on it (which annoys Paul to an extent). Meanwhile, Bridget has been constantly psycho-analyzing Kerry, which annoys her. So she gets back by telling Bridget that she has a disorder called narcissism.
Air date: 3/11/03
Kerry devotes her school video project to Bridget to illustrate the hypocrisy that life is much easier for the beautiful people. But when Bridget discovers that the video makes her look shallow, she takes Paul's advice to enrich her life by taking up tennis again, and ends up with a broken nose. Bob and Mike Bryan, the No. 3-ranked tennis team in the world, make a cameo appearance on the tennis court.
Good Moms Gone Wild
Air date: 3/25/03
While vacationing in Florida at Cate's parents' home, Paul and Cate catch Bridget and Kerry on the evening news partying with a group of Spring Breakers. But before a punishment can be implemented, the news runs archival footage that features a young, wild Cate letting loose in a bar, leading the girls to believe Cate is hypocritical. Meanwhile, a jealous Paul meets Byron, the man that Cate went out with during her college sophomore year, and Rory befriends Jake Fisher, an elderly gentleman whose stories about World War II turn out to be more fiction than fact.
Air date: 3/28/03
When Cate is offered a promotion at the hospital, Bridget is upset, as she depends on Cate to help her with her family tree project for school, while Kerry encourages her mom. However, when Cate is offered the promotion, she declines it, as it is too much stress on the family. It is revealed that Bridget wasn't really upset; she was just fooling Paul, and Kerry was trying to cover up the fact that she missed Cate. Meanwhile, Paul tries to introduce Rory to the world of baseball cards to take his mind off his monkey obsession. However, Rory manages to trade the cards for a monkey, which he names Kirk Gibson (possibly to fool Paul). The monkey remains hidden until the end of the episode, when everyone comes home and sees the mess the monkey made.
Queen Bees and King Bees
Air date: 4/4/03
Bridget and Paul are surprised to find themselves in similar situations when they are both alienated in their social circles. But they devise a plan to settle the score, leading Paul to crash a poker game with co-worker Tommy to get closer to boss Nick Sharpe, and Bridget trying to break up ex-boyfriend Kyle and her nemesis, Jenna.
Air date: 4/29/03
Bridget begrudgingly becomes a mother when she is assigned to take care of a baby made out of a sack full of flour for school. When Kerry and Rory bake cookies for the Great American Bake Sale to help put an end to childhood hunger in America, Bridget begins to notice that her baby is mysteriously losing weight.
The Doyle Wedding
Air date: 5/6/03
Much to the family's dismay, Cate invites the Doyles over for dinner, which turns out to be a stressful evening for all. Later, the Doyles invite the Hennessys to a wedding for their daughter. As the family always follows through on prior commitments, Paul tries hard to find an excuse not to go to the wedding. When Paul discovers that a play that Rory is in (in which he cross-dresses.) is on the same day as the Doyles' wedding. But when Paul gets ready to tell them they can't make it, the Doyles tell them that the Hennessys are like family to them. Paul changes his mind, and they go to the wedding, with Bridget and Kerry as the bridesmaids (they don't like the dresses, though), and Rory as the ring bearer. Meanwhile, Bridget has been avoiding Donny because she thinks he's dorky, but she ends up dancing with him at the wedding reception because she thinks he's now handsome.
Sort of an Officer and a Gentleman – Pt. 1
Air date: 5/13/03
Cate learns that her sister Maggie is having marital problems. Paul thinks the family can help her, so he invites her to stay at the house, much to Cate's dismay, as the two sisters have a history of sibling rivalry. Meanwhile, Bridget has become more mature after Paul and Cate let her go out with Donny, who is home from the Naval Academy. Bridget and Kerry believe that Kyle has ulterior motives when he befriends Rory.
Sort of an Officer and a Gentleman – Pt. 2
Air date: 5/20/03
The sibling rivalry between Cate and Maggie comes to a boiling point when Maggie gets a sexy new makeover and gives Bridget a water bra as a gift. Meanwhile tensions between the Hennessy sisters mount when Kerry and Kyle begin dating, while Bridget's popularity takes a nosedive after she dissed her friends for Donny, and Paul becomes concerned when he finds an empty pregnancy test kit, which turns out to be Cate's.