Joan invites their recently widowed neighbor, Gary Timpkins, to Thanksgiving dinner, during which everyone has a bad reaction to Colleen’s cauliflower dish. Also, Tim and Sophia try to find a last-minute replacement for Heather’s spoiled turkey, Jen and Greg debate who to name as Lark’s godparent and John takes Samantha to the Harvest Festival, where she sneaks into the corn maze with her boyfriend, Aiden.

Greg feels threatened by Jen's handsome assistant; Tim and Heather plan a prank.

The first season concludes with John and Joan revealing a shocking secret they've kept from their kids for 35 years. Also, Greg quits his job after creating a public funding campaign for his own invention. Heather and Tim try to make up for missing Samantha's Student of the Month Ceremony at school, and Matt's plan to make a big announcement at his and Colleen's book party keeps getting delayed.

When Tim accidentally shaves off a huge chunk of eyebrow before an important photoshoot, he hopes Jen and Colleen's grooming expertise can fix it. Also, when Gigi passes away, Greg makes an anonymous donation with the money she left him, but later realizes he wants to be recognized for it; John learns firsthand what Gigi's life was like at the nursing home; and Joan honors her mother's memory with unusual jewelry.

Heather freaks out when Samantha auditions for the high school musical and the director doesn't give her the part. Also, Matt, Greg and Heather suspect Joan is having an affair, and Tyler and Clementine decide to find a home of their own.

The Short family's quirky history is revealed with stories of when Tim met Heather's family for the first time; when Jen and Greg bought their dream home; when Matt got sidetracked after he saw Colleen while waiting for a blind date; and John's last flight before retiring.

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.