Sean blows his shot at snagging a loan from Claudia's dad (Stephen Root) after losing the car he gave Lily for her birthday in a street race. Meanwhile, Henry and Jimmy put the squeeze on their grandfather for some hefty Tooth Fairy funds.

Claudia's father, Tony, has returned to the Finnertys for and operation, and the rest of the family is very sympathetic, except for Sean.

Sean joins the Knights of Hibernia in order for Lily to compete in their beauty pageant.

Sean forgets to give Claudia an important message from her professor; Jimmy hides the telephone bill to conceal his calls to a 976 number; Lily freaks out when Brad doesn't call her for three hours.

Sean winds up in jail for buying some shady diamond earrings for Claudia from Eddie's so-called ""connection""; Lily protests the nuns's donkey-basketball game.

Sean has a hard time fighting off an amorous Claudia after lying to her that he's finally undergone a vasectomy. Meanwhile, Brad gets a chance to hang out with Lily by paying her to tutor him in a subject he already excels at.

Claudia wreaks havoc at a wedding reception after losing her glasses -- though it may not be Claudia who lost them. Meanwhile Lily convinces Eddie to persuade Dean to get her the perfect birthday gift; and Brad begins spending way too much time with Jimmy.

Eddie persuades Sean to help him break into his ex-girlfriend's apartment to steal embarrassing photographs.

Lily becomes insecure when she learns that she's ""not school smart."" So when Brad snags an interview at Yale, she becomes jealous and connives to land her own interview. Sean takes a second job as a limo driver, to avoid doing work at home. Claudia tries to convince her neighbor, Arianna, that the Finnerty clan is not trash. Jimmy seeks advice from his uncle Eddie for his debut in the school production of Tom Sawyer.

Sean inadvertently finds a fake ID in Lily's bedroom. Sean and Claudia confront their daughter about her rebellious behavior, but they get few answers. They decide to hack into her e-mail to find out more about Lily's trouble-making friends. While they are checking, an e-mail comes in from a ""SweetandNastee."" Sean responds, pretending to be Lily. SweetandNastee gives Sean an address to a rave party in Yonkers. Sean and Eddie go to the address which turns out to be a dry cleaners. Convinced the rave is really at the dry cleaners, Sean and Eddie try to gain access to the party but end up getting beaten up by the dry cleaners' owner. Back at home, Sean and Claudia confront Lily, but she slams them for invading her privacy. Turns out she knew they broke into her e-mail account because she was online at a friend's house when she saw her name logged in. Lily made up the rave to teach her folks a lesson about snooping.

Jimmy’s science project is late, because his parents made him go with them to a Ramones’ concert. When Sean pleads Jimmy’s case with the principal, he only succeeds in getting Jimmy thrown out of school.

Jimmy and his class are having a robot science fair. Sean goes all out to create a ""first place"" robot for Jimmy. When the judge of the fair calls Jimmy's robot ""substantial robot"" and ""you could prop a door wide open with this!"" Sean stands up and admits that he made his son's robot. He requests that the other parents do the same (It's obvious that the other robots were made by the parents.) In the end, Jimmy and his robot, fight Benji (his classmate) and his robot in a robot battle! Benji, who was marvelously acted wins!

The minor insults of Claudia's visiting parents get so far under an insecure Sean's skin that it starts to look like he's gone out of his mind. Meanwhile, karaoke leads to an unlikely liplock between Brad and Lily.

Sean and Claudia are shocked to learn that Jimmy has been shoplifting and try to figure out his motivations for stealing. Elsewhere, Lily agonizes over what to wear for dinner with Dean's parents. Brad helps her find the perfect outfit, but Dean's parents turn out to be not so great. Meanwhile, Henry brings home his class's pet lizard.

Lily goes on a shopping spree with her ""emergency credit card,"" resulting in her having to pay back the bill by getting a job -- at the bar. Meanwhile, Eddie fumes over a scathing review of the bar; and Henry takes energy preservation to the extreme.

Lily and Brad stress over their upcoming S.A.T. tests... and Claudia turns the SAT's into a competition. Meanwhile, Sean teaches Henry a lesson in compassion by taking in a homeless guy (Dave Sheridan).

After Eddie buys an electric car to impress a girl, Sean unwisely gives Eddie a loan without telling Claudia, which results in her college enrollment check bouncing. Meanwhile, Brad discovers a tatoo with Dean's name, but Lily's plea for her parents to pay for her tattoo removal goes ignored.

Sean talks to Jimmy about the birds and the bees; Brad accidentally sees Claudia naked.

Sean becomes jealous when Claudia is asked to do some modeling for a fashion photographer. So she storms out, leaving him to deal with a bath products party that she'd organized. Meanwhile Lily recieves her yearbook photos, which are terrible.

Sean and Claudia try to take advantage of an empty house and spend some alone time together; Lily realizes that Brad is not a good dancer.

Brad's (Bret Harrison) dad, Dan (guest star Gregory Jbara), claims to have been taking tennis lessons for years, however, after Sean (Donal Logue) beats him at a tennis game, it is revealed that Dan has been having an affair and not taking lessons.

In a desperate grab for attention, Lily makes out with the nerdish next-door neighbor, Brad O'Keefe, in his car; when Sean catches them, he responds in a rather unorthodox way--by throwing fried chicken at the windshield. Meanwhile, Walt babysits Jimmy and Henry and teaches them how to dig a hole; and Eddie tries to hook up illegal cable so he and Sean can watch softcore porn.

Jimmy's claim of demonic possession and Lily's skirt length prompt Sean's perceived battle with school head Sister Helen

Lily freaks out when Sean says they can't afford to send her on a ski trip with her classmates. But things get worse when she learns that Sean inherited some money and spent it on a guitar for himself.

Claudia is looking forward to a trip to New Jersey to try to bond with Lily. However, things go from bad to worse when Claudia tells popular cheerleaders from Lily's school that her daughter is still a virgin. Lily takes off, leaving Claudia stuck - with no daughter, no luggage, and no clothes.