Season 5

Brad, after admitting he hooked up with his space camp buddy, Lana (guest star Mila Kunis), begs for forgiveness from Lily until he learns of her infidelity.

Sean's feeling sick, and Eddie convinces him that he has sympathetic pregnancy syndrome. Brad and Lily decide to just be friends but their hormones get the best of them. Jimmy tries to impress the new neighbor girl by pretending to be a sports fanatic. Eddie resumes his relationship with his ex, Faye, who's become more bitter and angry than ever.

Now that Eddie is spending all of his free time with Faye, lonely Sean finds every possible thing wrong with her, including the way she parks her car, which he ""accidentally"" smashes into. Meanwhile, Lily's attempt to make Brad jealous by dating Mocha Joey backfires when Brad points out that Lily and Mocha Joey have nothing in common; and Claudia gets upset when she finds out that Sean has told everyone that she is pregnant.

Eddie moves into the Finnerty basement after being evicted from his apartment. Claudia is not happy and tells him if he screws up he's out. Lily is jealous of Taya, Brad's new girlfriend, after she becomes the first girl on the Football team at school. Claudia's pregnancy interferes with her motherly duties.

Claudia is upset with Sean when she finds out he gambled the money for the baby's crib and used the winnings to buy a new TV. When Claudia accidentally breaks the TV, she convinces Eddie to bring her to the track so she can win money to repair the set. Meanwhile, Jimmy must endure a painfully long day of father-son bonding to keep Sean from finding out about the broken TV, and Lily enrolls in a Big/Little Sister program, but is dumped by her Little Sister.

Brad and Lily fight it out in a race for student body president...but it seems all the sniping and mudslinging is a mask to hide the former lovers' true feelings about each other. Meanwhile, Eddie is depressed and seeks the help of a quack psychiatrist...and Claudia tries not to learn the baby's sex, wanting to be surprised.

Sean's old friend Dave is in town, a children's performer who goes under the name ""J.J. Bodybuddy"". He lets Dave stay at his house...but it isn't entirely altruistic. He's promised the school that he can get J.J. Bodybuddy to do a show for the kids. The problem is, Dave--a recovered alcoholic who hasn't touched the stuff in ten years--gets too drunk to do the gig, and Sean has to put on the Bodybuddy leotard hismelf. Meanwhile, Lily is jealous of the new baby, and is letting her feelings be known vociferously.

With the bar in financial trouble, Sean and Claudia are having difficulty paying their bills, so Sean applies for a manager position with T.J. Shenanigans, while Claudia works from home collecting unpaid medical bills. Sean and Eddie contemplate selling the bar after finding out that they are competing for the same job. Meanwhile, Brad and Lily get back together, to the dismay of broken-hearted Taya. On the rebound, Taya starts dating Jimmy to help win Brad back.

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 becomes infuriated after receiving letters from the Home Owner's Association telling him to clean up his house, while Claudia is happy about the positive changes to the neighborhood. Meanwhile, Lily insists that Brad buys her an anniversary gift from a list that she's made... but he defies her wishes and gets her a sexy nighty... that he can't enjoy because he's busy picturing Sister Helen, who he ran into at the lingerie store. And Jimmy shocks the family by making an unusual lifestyle choice -- he announces that he's a vegetarian.

Eddie's ex, Amy, displays naked photos of him in an art gallery, but he's too afraid to ask her to remove them... because she's crazy! Meanwhile, Sean is having problems trying to sell the Red Boot; Claudia has a baby shower; and Jimmy fills in on the cheerleading squad to get close to the girls.

In the series finale, Claudia and Sean miss Lily's graduation (thus spoiling Lily's senior-prank plan) when Claudia goes into labor. Meanwhile, the Finnerty boys learn that Walt has a girlfriend... his cleaning lady!