Duncan runs for class president against Mia, but soon realizes the competition is more than he bargained for. Meanwhile, Kimberly participates in a cookie fundraiser. However, when she pulls a sneaky trick, she quickly learns what goes around, comes around.

Annie feels underappreciate on Mother's Day and adopts Duncan's friend, Wolf, who seems to care more about her than her own kids. Meanwhile, Jack tries to make amends by finding Annie a rare flower.

After realizing their children are too dependent to even be left alone, Jack and Annie decide to implement "Free Range Parenting," by giving their kids more responsibility. So, Duncan and Kimberly are tasked with a simple grocery trip.. and somehow wind up in Mexico.

When their local swimming pool is overcrowded due to a heatwave, Annie and Jack share their old swimming spot with the kids. Everything is awesome, until a rich resident buys the land, drains the swimming hole and takes the kids to court for trespassing. Then, Annie's court confrontation with the rich resident leads to her getting her own public access court show.

When all of Jack's customers are stolen by sexy new plumber Bobby Bastille, he quits his day job to follow his dream and write a rock opera. He casts his family and books the town theater for a live performance, which Annie tries to nix. However, Duncan and Kimberly side with Jack, when they think the show might score them points with their crushes.

To celebrate their anniversary, Jack and Annie rekindle the passion of their youth by visiting a 1980s-themed club, before realizing that their maturity might not be that boring after all. Meanwhile, Jing makes Duncan "marry her," but their make-believe quickly becomes complicated by real marital problems. Also, Kimberly feels ignored and acts out for attention.

When the family gets a new smart fridge that turns out to be too smart for Annie's liking, she feels replaced. Jack and the kids see no harm in the fridge's increasing invasions of their privacy, until they realize that the appliance company that sold them the refrigerator has questionable motives.

The town celebrates its annual Witch Day, which involves pronouncing a mortified Duncan the "town virgin" for the big ceremony, but he protests the celebration to impress Mia, who finds it sexist and barbaric. Meanwhile, Annie and Jack steal a dead woman's chili recipe to try and win the celebration's chili cook-off.

Annie ropes Duncan into her investigation of a criminal selling counterfeit goods. Jack ends up making Kimberly and Jing violently ill in his attempt to be a cool dad.

Duncan's friends replace him with Kimberly in their online video game tournament, so he joins the opposition to betray them and humiliate Kimberly. Meanwhile, Annie tries to force Jack to throw out all his old memorabilia cluttering the garage.

Wanting to impress Mia, Duncan asks his mom Annie to teach him how to drive.