In a desperate attempt for attention, Lily makes out with the nerdish next-door-neighbor, Brad O'Keefe, in his car. Sean, who went to get a bucket of chicken, is out walking the dog when he spies his daughter and the neighbor boy. So Sean responds in a very unorthodox way -- by lobbing fried chicken at the car. Elsewhere, Walt babysits Jimmy and Henry, and decides to teach them how to dig a hole. And Eddie stays in the house and tries to illegally hook up cable so that he and Sean can watch soft-core porn.
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, a model of the solar system, is due and he's eager to get back from the street fair to finish it. However, when Sean and Claudia find out The Ramones are playing, Jimmy's science project is forced to wait. Sean decides to write a note to Jimmy's principal, Sister Helen, to explain that he felt it was more important for Jimmy to attend the concert than to finish his science project. The note only ends up getting Jimmy suspended. To make it up to him, Sean and Eddie take Jimmy to the Statue of Liberty -- again with disasterous results.
Sean volunteers to referee Henry's soccer team and ends up making an unethical decision in the team's favor. Which in hindsight wasn't a great idea, when Henry gets an inflated ego. So Sean tries to make things right the following week by making an unethical decision in the opposing team's favor. . . Meanwhile, Lily flirts with the cute guy at the concession stand and the conversation leaves her walking on air. But when she starts to obsess over the introduction, she replays the scene over and over in her head, each time thinking that she made a bigger and bigger fool of herself.
After the family car goes missing one night, the Finnertys find themselves at an impasse: Sean is in mourning over the loss, while Claudia hopes to gain from a slightly inflated insurance claim. But when the battered remains of the car are towed to the house a few days later, it becomes clear that Lily has been covering her tracks about an ill-fated joyride -- and the reason why her parents have to buy the missing parts from Eddie's maniacal mechanic.
Claudia is shocked to find some racy pictures downloaded on Jimmy's computer, and insists that she and Sean confront him about it, but Sean wants to ignore the situation. Later, Sean confesses to Walt that he downloaded the pictures, and its not long before Claudia discovers that Sean is the guilty culprit. Meanwhile, Lily gives Jimmy a picture of Sister Helen which they doctor and use as an e-mail joke. But when the e-mail is sent to Sister Helen, things aren't so funny anymore.
During a stressful day at work, Claudia takes a puff of a co-worker's cigarette which quickly turns into an entire cigarette and then a daily habit. Desperate to keep her smoking habit from Sean and the kids, Claudia tries her best to smoke without being found out, but is busted by Lily. Lily makes a deal with her - she won't say anything if Claudia will get her a cell phone and Claudia agrees. Sean thinks that Claudia's bizarre behavior lately has something to do with him, prompting him to buy her the expensive armoire Claudia was admiring recently at the flea market. When her quest for a cigarette leads to her digging through the trash and landing outside Brad O'Keefe's window, she realizes she has hit a new low and swears off her habit. Meanwhile, after setting a date with Dean on her new cell phone, Lily is humiliated to find out Dean heard her gushing about him when the phone didn't turn off.
After Henry unexpectedly catches Sean and Claudia having sex, Sean is determined to handle the inevitable topic of the birds and the bees with Henry in a better way than Walt did with he and Eddie. After having a father/son talk with Henry about sex, Sean feels good about how he handled things. When Sean and Claudia catch word that they have a ""reputation"", they discover that Henry told his entire class about what he caught Sean and Claudia doing, forcing them to do some damage control.
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!
Sean's takes a swing at tree surgery and ends up causing a blackout during the superbowl. But his biggest concern is what he saw through Lily's window while chopping the tree -- Lily holding a bag of pot. But what's even more shocking is where Lily got the weed: out of Sean's closet. With the blackout, Dan O'Keefe moves his Superbowl party to the Finnerty home, where they listen to a play-by-play given by Jimmy from his 5-inch TV.
While Sean and Claudia are chaperoning at Lily's school dance, Sister Helen catches Lily and Dean red-handed with a bottle of liquor while they are making out. Lily insists she is innocent and that the booze is not hers. But it comes as a surprise to both Lily and Sister Helen when the real culprit is revealed. Meanwhile, Eddie has taken to using Walt as his goon to shake down his shady business associates.
When Sean and Claudia win a free weekend in Atlantic City, Eddie offers to look after the boys while they are away. At first suspicious of his offer, they succumb because they desperately want the time away. But when they return from their trip to find Jimmy and Henry locked in the basement, they are shocked to find out that it was Lily and not Eddie who put them there. As Lily tries to explain what happened at home over the weekend, it becomes clear to Sean and Claudia that, surprisingly, Eddie was not such a bad choice to take care of the kids after all, even if he really did have an ulterior motive.
Claudia learns the results of her pregnancy test and Sean celebrates the news with a major purchase: a bar that Eddie plans to burn down for the insurance money. Meanwhile, Lilly and Brad try their luck at getting liquored-up; and Henry develops a craving for a different kind of watering-hole delicacy.
For the second time, Lily has failed her behind-the-wheel exam. But this time it's not her fault, it's Sean's, who went out of her way to sabotage her driving test by teaching her rediculous driving tips, such as the all-important ""W-turn."" In other events, Claudia is having a devil of a time keeping Henry and Jimmy from playing a violent video game condemned by Sister Helen -- but she winds up addicted to it herself.
The boys mock Sean when he can't get the lugnuts off of the car, leaving him to have his wife attract a trucker's attention to change the flat tire while he sits in drag in the backseat. Elsewhere, Eddie holds a garage sale at Sean's house where he sells off hot merchandise and his brother's possessions, and he welcomes the kids to partake in the sale. But Lily is mortified when Brad buys her old bra from Eddie, then boasts to the school that he and Lily have slept together.
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.
When the dump closes, Walt finds himself with an abundance of free time and begins hanging around the house, much to the dismay of Lily, who finds it increasingly hard to get alone-time with Brad. So she schemes to get him a date online... which turns out to be with a drag-queen. Meanwhile, Eddie finds out that his girlfriend has another boyfriend.
After Sean confronts Brad's father, who's boasting that Lily and Brad have slept together, he confronts Claudia -- and finds out she already knew too. So when Brad mysteriously gets injured by an airborn Christmas decoration, everyone thinks Sean finally lost his temper. Meanwhile, the boys have spent Sean and Eddie's Liberty quarter collection, and Eddie is disgusted. So Eddie takes the boys out to teach them a lesson about stealing from other people -- by stealing a toy machine that Henry loaded with quarters.
Claudia feels it's time to smooth relations between the two families by having the O'Keefes over for dinner, but the evening falls apart when Brad's mother blames Lily for taking Brad's innocence. Meanwhile, Eddie teaches Jimmy and Henry a lesson in respecting other people's property after he finds out that they used his coin collection to play arcade games.
Sean and Eddie hire strippers for the bar to help make ends meet -- then wind up being protested by the PTA. But what's most shocking is who set the PTA on their tails. Meanwhile, Brad asks Lily to break up with Dean. Lily doesn't want to hurt Dean, but agrees, only to find that he takes it far easier than she expected.
Brad is bothered that Lily is embarrassed to be seen with him, so Sean tries to make over his geeky image. But all Sean succeeds in doing is inadvertantly getting another student suspended from school... Which leads to an in-bar confrontation with Sister Helen. Meanwhile, Jimmy's ""trademark"" hair-length has become an issue at school. Elsewhere, Claudia helps Eddie deal with an unwise purchase he made for the bar -- by getting drunk with the customers. And Lily confesses her relationship with Brad in front of the entire school.
After a night of partying, Lily wakes up with a nasty hangover, her car parked on the porch and no memory of how she got home. To teach Lily a lesson, Sean and Claudia decide to sell her car and have her sign a contract that she will call them when she is too drunk to drive. Angry at losing her car, Lily pretends to be drunk night after night in order to make her parents give her a ride home. Meanwhile, Eddie makes a huge profit when he sells Lily's car for Sean.
When the Finnerty's throw Brad a birthday party to take his mind off his parents' recent breakup, Sean secretly invites Brad's dad to the party as part of his ""plan"" to reunite him with his wife Connie (guest star Nancy Cassaro). Unfortunately, Connie has taken Claudia's (Megyn Price) advice to ""get some,"" which prompts her to pursue Eddie.
This one might be better: Sean is having trouble keeping the bar alive and Claudia asks him to reconsider running it. With St. Patrick's Day around the corner Eddie tries to lure customers over from rival pubs. Meanwhile, Brad and Lily prepare for the parade and Jimmy is having trouble understanding the meaning of St. Patrick's day.
Claudia tries to alleviate Sean's hypertension and high blood pressure by running the household all by herself but everything goes awry. Jimmy gets suspended from school, which causes a set of problems all its own, and Lily and Brad break her bed so they steal the family car... and get it impounded.
Lily is less than thrilled about Brad's new job, which is taking up all of his time. Meanwhile, Walt's having problems finding work, so Sean and Eddie offer him a job at the bar... but they soon find that he takes over. Jimmy's at the age where he finds his mother to be an embarrassment, so Claudia sets out to bond with him.
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.
Depressed that she doesn't feel sexy while pregnant, Claudia gets a boost when her cute study buddy, Steve, flirts with her. But her bubble is burst when she finds out that Sean paid him to do it. Meanwhile, Lily helps Eddie write material for his stand-up routine, but it backfires when another comic steals Eddie's jokes. Brad gets a reluctant Jimmy into Sciencenauts and his attitude changes when he finds out that the ""secret"" of every meeting involves porn.
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.