Tim thinks wearing a Cinderella dress during March Madness is good luck, so he refuses to take it off in hopes his alma mater will win. Also, Greg fantasizes about what to write in a birthday card for his boss, Tyler goes to prom and must withstand unsolicited advice from his parents and grandparents, and Jen sets Matt up on a blind date with her coworker, Dougie.

In the second season opener, Heather and Tim ask Clementine's parents to convince Clementine and Tyler to get a marriage annulment; Matt moves in with Colleen, much to the dismay of her roommate; John takes the wrong dose of his daily pill, which leads to complications.

When Joan's creative writing teacher, Professor Sinclair Wilde, praises her work, John assumes it is because he has a crush on her. Also, Tyler and Clementine invite Matt and Colleen over for an awkward dinner party; Jen tries to hide it from Greg when Lark takes her first steps while he's away on a business trip; and Colleen, Heather and Jen take Dougie out for ladies night when she realizes she might be gay.

Matt and Colleen experience crazy sleepwalking adventures after taking a sleep aid; Jen tells Greg she had a sex dream about a family member; Tim wants to help Sophia get through a slumber party; John installs a motion-sensor light in the yard.

When Colleen goes to Tim for help with an embarrassing ailment, she begs him not to tell the family. Also, Dougie enlists Joan to help her buy a gift for Matt and Colleen's wedding. Heather gets jealous when her friends want to include Jen in their group.

When Matt is in a hurry to get to the fertility clinic, each member of the family has a crisis that prevents him from getting there on time.

After John befriends the janitor at Sophia’s school, Mr. Sissel, John learns that Sophia and her friends believe a childish rumor about him. Also, Heather pushes Tim and Joan to go for walks together while recovering from their health issues; Matt and Colleen try to tame Dougie’s bad habits; and Jen is desperate to not go into labor during Lark’s birthday party.