After Matt walks in on Joan and John being intimate, Joan attempts to lead a group therapy session. Also, Jen hires a breast-feeding consultant couple, Matt and Colleen have the most enjoyable bad date ever, and Heather and Tim move to a new home with the help of a moving company that employs ex-cons.
When Matt invites Colleen to brunch with the family, he coaches her through the difficult task of connecting with them. Also, John, Matt and Greg try to prove their masculinity by cutting down a tree in Greg's backyard, Tim has an adverse reaction to espresso, and a sleep-deprived Greg has a run-in with the cops.
The siblings congratulate Greg after word spreads that he stood up to Joan for passive-aggressively questioning Jen’s parenting skills. Also, Chad insists on having one last meal with Colleen’s grandmother before heading off to jail, Matt and Greg discourage Tim from beating John at a round of golf and Sophia gets a peanut stuck up her nose.
Tim and Heather unintentionally make things incredibly awkward for Tyler when he brings his gorgeous new girlfriend, Clementine, to meet the family. Also, Matt and Colleen are caught canoodling at the office by their obnoxious co-worker, Will, Jen and Greg vow not to become germaphobes, and John buys Sophia a cell phone behind her parents' backs.
When Matt and Colleen catch Chad trying to kidnap her beloved pup, Princess, Chad uses the opportunity to pitch them his new business venture. Also, Jen and Greg try to be intimate for the first time since having a baby, Heather “breaks up” with her longtime hairstylist, Lynette, and Tim ruins Samantha’s birthday party.
When Jen and Greg interview potential nannies for Lark, they find it difficult to find one they trust. Also, Tim, Matt and Greg go camping, Heather suspects Matt bought Colleen earrings with money she loaned him, and John makes a wooden puppet for Lark that the family has more fun playing with than she does.
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.
When Jen cuts her finger and Greg takes her to the hospital, they finally have the first quality alone time they’ve had in months. Also, John takes Samantha and Sophia to a restaurant where everything is named after feelings, Heather gives Tim a sexy anniversary gift, and Sophia is punished after Heather hears her swearing.
Greg is still bitter over an accident that sidelined a competitive game of ping-pong he and Matt had started years ago, so they decide to finally settle the score. Also, Heather questions herself after urging Tim to get a vasectomy, Jen is stressed about returning to work, and Joan learns her credit card has been stolen after strange packages start arriving.
Colleen joins John and his Air Force buddies for his annual tradition of dirty Christmas caroling. Also, Joan tries to hijack Lark’s first Christmas from Jen and Greg, Samantha sneaks out with her friends and is caught when a photo of her and a mall Santa is posted online, and Tyler announces his plans for college,
Heather and Tim finally find another couple they actually like to socialize with, but Sophia and their son don’t hit it off. Also, Greg insists he and Jen take separate flights in case something happens to the plane, Matt and John take Gary out to meet women, and Matt’s ex-wife, Bonnie, surprises him with a visit
Greg joins Colleen's gym and goes overboard gearing up to work out. Also, Heather and Jen host a secret garage sale that directly competes with one Joan is having, Tyler and Samantha throw a party while Heather and Tim are away for the weekend, and the family has second thoughts about eating lobster for dinner.
When Greg and Jen slip away for a couples massage, the afternoon doesn’t turn out to be as relaxing as they expected. Also, Tim, Heather and the kids have a contest to see who can accumulate the least trash, Colleen asks Matt to illustrate a children’s book she is writing, and Jen helps Joan and John with their will.
When Joan's freewheeling nephew, Mikey, comes for a visit, the family members are on edge since nobody really likes him. Also, Tyler brings Clementine, to visit his great-grandmother, Greg and Jen find a solution to their sleeping woes, and Matt takes over for Tim as Sophia's soccer coach.
When Tyler and Clementine go to a guitar store, Tyler gets uncomfortable when the attractive salesman, Ian, repeatedly hits on her. Also, Tim’s tattoo artist, Lois makes a spelling error on a tattoo he got as a Valentine’s Day surprise for Heather, Matt’s plan to celebrate Valentine’s Day with Colleen doesn’t go as well as he hoped, and Greg and Jen discuss whether they should have another baby
When John starts feeling old, he attempts to make himself look younger, much to the dismay of his family. Also, Heather worries that Sophia’s piano recital will be a disaster; Jen, Greg and Lark go to an over-the-top birthday party full of overachieving parents who make them panic about getting Lark into a good preschool; and Matt meets Colleen’s mother, Mia, for the first time.
After realizing that Sophia is growing up faster than he’d like, John buys himself a pet, but it doesn’t get along well with Joan. Also, Heather accidentally sends Tyler a sexy text message, Jen and Greg try to help Samantha win her boyfriend back and Heather and Jen console Colleen and Matt over their break-up.
John and Joan disagree with their neighbors, Jerry and Pam, about who gets to use the hot tub when new property lines are drawn. Also, Greg and Jen invite their exterminator and his wife over for dinner, Matt and Colleen make an effort to be friends, and Tim is terrified to perform minor surgery on John.
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.
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.
