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Accomplished actors Dianne Wiest and James Brolin star as the heads of a large, happy family, in which each member is approaching different milestones. Their eldest daughter, Heather (Betsy Brandt) and her husband consider having another child as they get closer to an empty nest; middle child Matt (Thomas Sadoski) thinks he has found true love; and the youngest of the three siblings, Greg (Colin Hanks) is overwhelmed after having his first child with his wife. Various perspectives are employed as each family member's story unfolds.
The Hughes move into John and Joan's home after their kitchen is destroyed. John tries to get Sophia back on track when she starts misbehaving.
Jen and Greg can't remember Jen's boss's wife's name, Tim urges Tyler to start dating, and Joan's stress grows about living with Heather.
Heather finds a map to a time capsule she buried with her brothers as kids, Joan joins her neighbour's poker game, and John finally gets hearing aids.
When Heather, Clementine and Jen offer to save Joan from the stress of preparing the Thanksgiving meal, the free time leaves Joan even more frazzled.
Tim and Heather are determined to finish an expensive dinner as they celebrate their anniversary. Meanwhile. Matt and Samantha go to a trapeze school.
Heather tries to become Tyler's best friend, while Tim goes overboard while keeping a watchful eye on Samantha and her boyfriend.
Jen and Greg hire Clementine as a part-time nanny for Lark, Tyler's new girlfriend turns out to be Sophia's teacher, and Matt gets frustrated with Colleen.
Christmas is just around the corner and, as in every family, the spirit of this time expresses itself in different ways with the members of the Short family.
Sophia asks Matt and Colleen about having children, Jen and Greg's new neighbours aren't as nice as they seem, and Heather interferes with Tim's hiring process.
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.
Jen sings in Tyler's band and gets caught up in the excitement, creating an awkward situation for him. John and Greg decide to brew beer together.
Greg and Jen's crazy neighbours invite them to a party, but Greg lies to get out of attending. Sophia decides to shave her legs.
Matt drives Greg to a job interview, but they encounter bizarre obstacles along the way. Tim bribes Samantha to attend traffic school.
Jen and Greg deal with her visiting parents, Heather runs into an old flame while chaperoning Samantha's dance, and Sophia loos into the family lineage.
Sophia feels like she is no longer the cutest kid in the family and tries to regain her status. Colleen and Tim bond when he helps her with hormone injections.
Colleen babysits Lark, and Jen comes home to find her dolled up in Colleen's old pageant dress. Joan's bike is stolen from the driveway.
Jen and Greg go to great lengths to find the perfect babysitter for Lark, and Heather learns something about Samantha's boyfriend she isn't sure she should reveal.
Jen is offered a custom painting as payment from a artist, but doesn't like the final product. Sophia convinces Matt and Colleen to use her idea for a book.
The Short family's quirky history is revealed. Tim meets Heather's family and Matt is sidetracked by Colleen while waiting for a blind date.
Joan asks Jen for a recipe to add to the family cookbook, prompting Jen to steal one from her favourite restaurant. Tyler and Tim are asked to buy a bra.
Jen and Greg get surprising news, while Colleen and Matt send out a video thank you message for their wedding gifts, irritating the family.
Tim and Heather plan a surprise party for Samantha, but the night takes an unexpected turn when she doesn't come home alone. John and Joan decide to learn Spanish.