Duncan avoids summer school for the first time, and the family goes on vacation. On their getaway, Annie and Jack are haunted by another vacation couple, while Duncan agonizes over Mia's Instagram, and Kimberly gets a glow-up.

Duncan says the one thing no kid should ever say to their dad, which shifts their power dynamic and forces Jack to confront his own father. Meanwhile, Kimberly and Jing have a window to do whatever they want, as Annie and Jack deal with Duncan's issue.

Duncan starts racing stock cars to get away from his mom, but it turns out they make a great racing team. Jing demands a room renovation, so she can secretly spend more time with Kimberly, while Jack struggles with the project.

Jack and Annie hijack a middle school party thrown by the cool kids, to which Kimberly wasn’t invited. They then devise a plan to get the kids to their house, so Kimberly can “up” her popularity game, but things get out of hand. Meanwhile, Duncan and his friends work on creating a viral video, so they can become the next internet sensations.

Annie battles the city mayor for the town's prestigious Oakie Award, when she refuses to remove the parking boot from the Mayor's SUV. The rest of the family grapples with the fallout from Annie's struggle, when the Mayor retaliates.

Jing and Jack start a child birthday band together and Annie takes on managing them. Meanwhile, Duncan and his friends try to raise money to buy a massage couch they tried out at the mall, by charging scooters.

Jack coaches Jing's little league soccer team, but when he feels he's too easy on the kids he calls on Duncan to yell at the team to get them to win. Meanwhile, Annie takes Kimberly to work with her after she has a falling out with her friends.

Duncan skips the PSATs to hang out with his grifter Uncle Stan, to the disappointment of Annie and Jack. Meanwhile, Jack, Kimberly and Jing clean the creepy attic to stay on Annie's good side.

Kimberly gets her braces off and finds new popularity. Jack accidentally has his ponytail cut and embraces his new persona of authority.

Annie is suspended from her job and bonds with a group of birds that ends up invading their home. Kimberly tries to call a boy and Duncan wants to jump to a high branch.

At the annual Witch Day Festival, Kimberly mixes up a magic witch potion that actually works, causing Jing to become possessed. Duncan and his friends enter a haunted Circuit City and Jack tries again to finally win Annie a stuffed animal at the milk bottle toss.