Lily overanalyzes a postcard Brad sent from space camp and worries that he's cheating on her, so she kisses another guy for revenge. Elsewhere, Sean thinks Claudia's pregnant after he answers a phone call from her doctor, but he's scared to tell her the news; Eddie tries his hand at stand-up comedy and Jimmy wants to join him on the road. Lana: Mila Kunis.
Sean's feeling sick, and Eddie convinces him that he has sympathetic pregnancy syndrome. Also: Brad and Lily decide to just be friends, but their hormones get the best of them; Jimmy is smitten by a new neighbor; Eddie starts dating a former flame (Karri Bowman) and finds that fighting with her keeps their relationship healthy. Taya: Arielle Kebbel.
When Lily finds out that Brad's been spending a lot of time with their new neighbor, Taya (Arielle Kebbel), she tries to make him jealous by dating Mocha Joey (Ryan Devlin)---again. Elsewhere, Claudia's mad at Sean for being the first to tell everyone she's pregnant; and Sean doesn't like Eddie's new girlfriend, Faye (Karri Bowman), so suspicions are raised when he “accidentally” backs into her car.
Evicted---yet saving for a house---Eddie moves into the Finnerty basement; Lily wants to give Brad's new girlfriend (Arielle Kebbel) the boot; Claudia's pregnancy interferes with her motherly duties. Sister Helen: Miriam Flynn.
When Claudia accidently breaks Sean's new TV---which he bought without her approval--- she fears he'll think she broke it on purpose. Elsewhere, Lily looks after a “Kid Sister” (Miranda Cosgrove) as part of a school caregiver program.
Eddie sees a therapist (Scott Thompson),who tells him that Sean is the source of his problems. Elsewhere, Lily runs for student council president to get back at Brad, who's also running; and Sean wants to know the sex of the baby, but Claudia wants it to be a surprise.
Sean gets his old friend Dave, a semi-famous kids' entertainer, to agree to perform at an annual school fair, but Dave disappears the day of the event---and Sean is partly to blame. Also, Lily gets upset when she learns that she'll have to share her room with the baby, so she threatens to leave home and join a singing group that is touring in Japan. Dave: David Frederic Herman. Carolyn: Alessandra Toreson. Sister Helen: Miriam Flynn.
Sean plans to sell the bar and take a managerial job at another pub, but he discovers that Eddie's applying for the same position; Claudia begins working as a bill collector; Lily gets suspicious when Taya and Jimmy start dating. Taya: Arielle Kebbel.
Pregnant Claudia is feeling unattractive, so Sean pays her college study buddy (Trent Ford) to hit on her so she'll think she's still sexy. Elsewhere, Brad accepts Jimmy into the Sciencenauts club, even though Jimmy never asked to join; a comedian rips off Eddie's stand-up routine.
Sean gets a part-time job as a limo driver and complains to Claudia that it's tough work so he can shirk his other responsibilities. But Claudia finds out he's lying when she visits him on the job. Meanwhile, Lily wants to get into Yale because Brad plans on going there, so she lies on her application; and Eddie helps Jimmy prepare for a part in a school play. Arianna: Dana Wheeler-Nicholson. Mr. Kersey: Chris Hogan. Becky: Shannon Collis.
Sean is forced to fix up the house when a neighborhood association sends letters threatening to fine the Finnertys for the poor appearance of their home. Later, he discovers the real source of the letters. Also, Jimmy reveals to Eddie that he's a vegetarian; and Brad buys Lily a sexy camisole, but when he sees her wearing it, he thinks of Sister Helen, who was at the store when he bought it.
Eddie's former girlfriend (Elizabeth Berridge) displays naked pictures of him at an art gallery, but he's afraid to tell her to stop because he thinks she's crazy. Meanwhile, Sean has trouble finding an investor to buy the Red Boot and tells Eddie to persuade his ex to buy the place; Jimmy fills in on the cheerleading squad to get close to the girls.
Sean and Claudia miss Lily's graduation (and throw a wrench into her senior-prank plans) when Claudia goes into labor. Elsewhere, Sean and Eddie learn that Walt has a girlfriend (Gina Gallegos), who happens to be his cleaning lady. Prof. Gollin: Allan Trautman.