Sean finds out that Lily slept with Brad when he learns that Brad's father has been bragging about it, and is upset that Claudia knew as well. Meanwhile, Eddie sets out to teach the boys a lesson about stealing when he finds that they've spent his and Sean's collection of liberty quarters.
Sean and Eddie make ends meet by hiring strippers for the bar, only to find that the PTA is hot on their heels with complaints. Meanwhile, Lily agrees to Brad's request to break it off with Dean, but he seems to take the news surprisingly well.
Brad is upset when Lily is ashamed to be seen with him in public, prompting Sean to try to transform him from geek to sleek. When this only makes matters worse, Sean gets an earful from Sister Helen. Meanwhile, Claudia helps Eddie get over a bad decision he made regarding the bar by drinking with the customers, and Jimmy's hair is deemed inappropriately long for school.
Brad's plan to make a romantic date for Lily in New York City go awry, while Henry decides he may have found a new pet when it crawls though a window Eddie broke in the house.
Lily and Brad fret over the upcoming SATs, which Claudia turns into a contest between the two. Meanwhile, Sean opens his door to a homeless man to show Henry a little something about compassion for others.
Eddie buys an electric car to win over a girl, which leads to Sean loaning a strapped-for-cash Eddie some money, an act which causes Claudia's college tuition payment check to bounce. Meanwhile, Lily wants to get a tattoo containing Dean's name removed to appease Brad, but her parents won't help her with the money.
Lily wakes up after a night of carousing to find herself hung over and her car parked on the lawn, with no memory of what happened. Sean and Claudia teach her a lesson by selling her car, which nets Eddie a big profit, and forcing her to sign an agreement stipulating that she call them when she is too drunk to drive. Lily retaliates by pretending to be drunk every night.
Sean decides to have a talk with Jimmy about the birds and the bees. Meanwhile, things get awkward for Brad with Lily and Claudia after he accidentally sees Claudia naked.
Sean has a touch of envy when Claudia is recruited by a fashion photographer for some modeling work, and Claudia decides to leave and let him to take on the bath products party she was to host. Meanwhile, Eddie helps comfort Lily when she is sent her less-than-flattering yearbook pictures.
After the bar is robbed, Sean starts to think Eddie is the culprit after he shows up with some new choice possessions, leading Walt to tell his sons that, in reality, his date handcuffed him to the bar and robbed the place. Meanwhile, Lily meets a cute guy while shopping, and Jimmy is hot for his new girlfriend.
Sean is forced to give up going to a rock concert to look after Henry and Jimmy while Claudia goes to a study group. He later finds out she was actually partying with Lily, but she then finds out that Sean then dumped the kids on Eddie, who in turn dumped them on his newly-hired security escort.
Brad invites Dean and his new girlfriend to come to Lily's party, but Lily has a hard time accepting the fact that he's gotten himself another girlfriend so fast. Meanwhile, Eddie tries to do some standup at the bar, but his most successful bits come from dishing the dirt on Sean and Claudia, while Henry screws up Jimmy's chances with one of Lily's friends.
Sean forgets to give Claudia a vital message from her professor about a test, but when he tells the professor out of guilt, he learns she already got to retake it. Meanwhile, Lily panics when Bret doesn't call her for hours, and everyone learns the phone is down because Jimmy hid the bill after making some risque hotlines.
When Claudia and Sean take a getaway and watch a porn film at their hotel, they recognize the shooting location as their home, which angers Claudia when she realizes Eddie was behind it all. Meanwhile, Jimmy is bullied by a girl at school who may, in reality, actually like him.
Things go awry when Claudia and Sean take a night of relaxation at home at the hands of a masseuse. Meanwhile, while watching Jimmy and Henry, Eddie helps the pair to express their frustrations with one another, and Lily's date to a formal with Brad gets awkward on the dance floor.
Lily, Jimmy, and Brad, sign abstinence agreements at school, but when Sean tries to counsel Brad to make sure he stays faithful to the agreement, Brad decides the best way to do so is to propose marriage to Lily.
Though Brad's father, Dan, claims to be a great tennis player, Sean beats him easily and inadvertently learns that he's really been having an affair during all that tennis lesson time. Sean tries to get Dan and his ex-wife, Connie, back together at a birthday party for Brad, only to discover that she's begun sowing some wild oats by chasing Eddie.
Claudia gets upset when she learns that Walt gave her spot in the family burial plot to his deceased cat, while Lily is upset that Claudia won't let Brad into the family photo. Meanwhile, Eddie worries that his ex-girlfriend will break up his new relationship using some questionable photos of him and enlists Sean to help him get the pictures back.
Sean and Eddie plan a huge St. Patrick's Day bash at the bar, but when the celebration day comes, the two realize they don't have any beer handy. Luckily, a skeptical Claudia comes to the rescue with beer in tow. Meanwhile, Brad and Lily design a nice leprechaun float for the annual parade, but the crowd freaks out when it accidentally gets ruined.
Sean finds himself in the position of having to discipline one of Henry's unctious friends. Meanwhile, Lily forces Brad to decide between being with her or hanging around his uncool friends, and Eddie tries to find love on an online Jewish singles site.
Claudia copies one of Lily's papers for her college course, but she soon finds out after the fact, to her dismay, that Lily had actually plagiarized the paper herself. Meanwhile, Eddie shows Jimmy the right way to unhook a bra.
When Claudia's dad Tony comes for a visit, Sean proudly announces he's paying back the loan he borrowed years ago, only to learn that Tony plans to use it to get some cosmetic work done. Meanwhile, Jimmy decides he wants some space apart from Henry, while the IRS comes after Eddie.
Claudia takes charge at home when Sean tries to lower his stress levels to save some money on his health insurance, but things start to get out of control with Jimmy, Lily, and Brad.
Lily learns that Brad's job to help buy a car comes with a sacrifice of his dignity at the expense of a demanding boss. Meanwhile, Sean and Eddie hire their Dad at the bar, but Walt soon begins to scold them like kids again. Henry, meanwhile, begins to grate on the nerves of Eddie's new beau, while Claudia's attempts to get more in touch with Jimmy's life fail miserably.
Brad goes off to space camp for the summer to hang out with his camp friend, Lana, after Lily insinuates once too often that Lana doesn't exist. Meanwhile, when Hope confesses a secret about Eddie to Claudia, the secret travels and ends up getting back to Eddie via Sean.