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.
Heather and Tim enlist Clementine's parents to help persuade her and Tyler to annul their marriage, while Jen and Greg keep a secret from the family.
Greg avoids voting in the presidential election because the queue is too long - then lies to Jen about it. Heather begins working in Tim's office.
Tim accidentally shaves off a huge chunk of eyebrow before an important photoshoot, and he hopes Jen and Colleen's grooming expertise can fix it.
Colleen teaches Matt a thing or two about saving money. Tim tries to fire Heather, and John helps Sophia conquer her fear of flying.
Joan's creative writing teacher, Professor Sinclair Wilde, praises her work, and John assumes it is because he has a crush on her.
John's plan to make Samantha choose boxing over ballet has unintended consequences. Jen tries to get a second opinion about a tonsil surgery, and Greg grows a beard.
Colleen admits she cannot swim, so Matt tries to teach her. Tim tries to ruin John's audition tape for Survivor out of jealousy, and Heather gives Sophia 'The Talk'.
Colleen and Joan shop for wedding dresses, Clementine feels she has overstayed her welcome, and Jen struggles to stay awake after a romantic date night
The Shorts take a trip down memory lane, recalling John and Joan's party to celebrate the turn of the century.
Jen, Colleen and Tim secretly play Short Family Bingo during the weekly Sunday brunch, while Matt, Greg and Heather suspect Joan is having an affair.
Colleen and Matt hold a family party to watch the LA Rams in action, and when things get boring they invite a famous American football player to liven it up.
Matt is forced to tell Greg about the secret wedding plans, Colleen refers Jen to her aggressive bikini waxer, and Clementine gets a job at a car rental office.
Greg and Jan hire Allie to cook for them on Valentine's Day. Matt and Colleen want to adopt a dog, while John and Joan try to buy a classic car.
John and Joan join the world of social media, Tim gets tickets to the Grammys, and Matt and Colleen meet their wedding planner.
Jen and Matt have an awkward dinner without Greg and Colleen, and Heather and Tim try to sneak wine into an ice skating show.
Greg stirs up a family feud when he finds money he accused Matt of stealing, while Joan takes offence when Heather writes off her forgetfulness as old age.
Matt and Colleen have some sleepwalking adventures after taking a sleeping aid, Jen tells Greg about a sex dream, and Tim helps Sophia get through a slumber party.
Matt meets Colleen's maverick father Miguel and his latest wife to ask for her hand. Greg is upset that Lark only wants to be held by Jen.
Matt and Colleen have a terrible time babysitting Lark while Jen is at work, while John buys Sophia a butterfly kit for her birthday.
Colleen goes to Tim for help with an embarrassing ear ailment and begs him not to tell the family, Joan helps Dougie buy a gift for Matt and Colleen's wedding.
Greg and Jen take Lark on her first aeroplane trip, only for their parental skills to be upstaged by another couple travelling with their baby.
Colleen and Matt question if they will ever get married after missing all the flights to Mexico. The Hughes family have to move in with Tyler and Clementine.