Max tracks Sydney’s phone after he suspects she snuck out to a concert with Olive against his wishes. His parenting dilemma reminds him of his childhood when his mom paged him on his beeper incessantly to track his whereabouts.

Sydney and Olive struggle with their babysitting business when the little kid they’re hired to watch happens to be the brother of one of the most popular kids in their class.

Sydney is invited to a pool party but is self-conscious her legs are too hairy and contemplates shaving. Her predicament reminds her dad Max when he was eager to start shaving to prove his manhood.

Sydney and Olive are so excited for their weeklong sleepover but quickly learn being together 24/7 has its challenges. Max recalls when he and Leo had a fight about Max constantly forgetting his job responsibilities at the arcade.

Sydney is baffled when she can’t seem to get an A in her poetry class even though her dad got A’s in his class—and they have the same teacher, Mrs. Harris.

Sydney organizes a school protest for clubs to be more inclusive of women. Young Max befriends a skater girl but is conflicted because the Dog Boys don’t allow girls in their crew.

Sydney and Olive’s bond is tested when they both become friends with the new girl but try to keep the friendship a secret from one another.

Judy enlists Grandma Judy to help her redesign the basement into their very own “girl cave.” Max starts to feel left out when Sydney cancels their plans together to throw a 50s-themed party with her friends to celebrate her new space.

Sydney thinks her dad might be lonely, so she encourages him to start dating again. When Young Max breaks his skateboard again, Mom makes him earn money to buy a replacement.

Sydney and Olive decide to help Max at the bike shop’s biggest sale of the year. When Leo’s dad hires a girl to work at the arcade, Max and Leo compete to see who can impress her the most.

When Olive becomes class treasurer and accidentally loses the money for the ice cream truck she promised her class, Syd helps her get it back. Young Max offers to accompany his mom to a wedding but does not know how to dance.

Sydney surprises her dad Max for his birthday by inviting his childhood best friend Leo and his son to visit from San Francisco.

When Max realizes he needs an extra hand at the bike shop smoothie station, Sydney and Olive convince him to hire their crush, Zach.

Syd thinks she’s too old for the father-daughter dance, but she’s afraid to hurt Dad’s feelings. Young Max is bummed when his dad isn’t around for a father-son event.

Grandma Judy’s feelings are a little hurt when Sydney gets her ears pierced on an outing with Mrs. Harris.

When something embarrassing happens to Sydney at school, she barricades herself in her bedroom and ends up watching old VHS tapes of Max when he was a kid. Sydney eventually falls asleep and dreams that she’s in the 90s.

When Grandma Maya comes to visit, Sydney loves spending time with her so much that Grandma Judy feels a little left out.

When Sydney struggles with ballet, something her mom was great at, she starts to feel like she’s losing touch of her mom.

When a cell phone ban policy during school hours goes up for a vote, Sydney is sure her dad, who’s on the Parent School Committee, will vote against it.