Rita and Patty secretly submit an application for Kip to a performing-arts school and he's offered an audition. But Hallie is upset to learn it is a boarding school and blames her mother for trying to keep her away from Kip.
Rita's insecurities about her pregnant body heighten when she meets Jay's pretty new colleague Stephanie (Christine Lakin). Stephanie later reveals to Rita that Jay's been confiding in her about his new-baby fears. Meanwhile, old feelings resurface for Hallie and Kip.
Jay sees Rita's mother (Swoosie Kurtz) flirting with a man who isn't her husband. Meanwhile, Kip offers to teach Rita's neighborhood nemesis Jasper how to play the drums as a way to make money for college.
Rita worries about traveling to attend a work seminar because of Jay and her mother's constant bickering at home. With Rita away, the situation worsens when the two realize the garage door was left open and Rita's guitar has disappeared. Swoosie Kurtz guest stars.
Rita's judgmental mother (Swoosie Kurtz) comes for a visit, throwing Rita into a whirlwind of housecleaning and junk-food hiding. But when her mom arrives with a new relaxed attitude, Rita suspects something's amiss.
Hallie and Kip try to be friends after their breakup. Meanwhile, Rita and Jay befriend the parents of Shannon's classmate Brianna, but are caught in the middle when Shannon decides to end her friendship with the girl.
Hallie attends a college party without permission after Patty's son encourages her to pursue higher education. Meanwhile, bad feelings between Rita and Patty result in a lousy audition for the band, but the two come together to search for Hallie.
Budding designer Hallie's work motivates Rita to plan a fashion-show fund-raiser, but Rita has second thoughts when she sees the dress Hallie creates for her. Meanwhile, Jay takes his role as cup-stacking coach for Shannon too far.
Shannon's teacher (Jennifer Elise Cox) urges Rita and Jay to enroll their daughter in a school for gifted children. Meanwhile, at Rita's suggestion, a depressed Hallie signs up for a breast-cancer walkathon to take her mind off of being single.
Rita plays matchmaker for Patty, but when Patty declares she isn't ready to settle down, Rita sets out to prove that marriage isn't routine. She persuades Jay to go clubbing and makes sure Patty witnesses their married night out.