Sydney wants to radically change up her hairstyle for the first day of 7th grade. Her dad Max is resistant, but with Olive's help, Sydney takes matters into her own hands.
Sydney wants to adopt a dog, but Max doesn't think she's ready for that responsibility. A flashback to young Max reveals he also wanted a dog, but his mom gave him a pet turtle instead.
Max tracks Sydney's phone after he suspects she stuck 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 about how to deal with her leg hair; young Max is eager to start shaving to prove his manhood.
Sydney and Olive are excited for their weeklong sleepover; young Max and Leo get into a fight about Max constantly forgetting his job responsibilities at the arcade.
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 enlists Grandma Judy to help her redesign the basement into their very own "girl cave." Max starts to feel left out. Young Max and Leo decide to build fighting robots in the basement, but don't want Judy to find out about it.
Sydney thinks her dad might be lonely, so she encourages him to start dating again. When Young Max breaks his skateboard again, Judy 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, Sydney helps her get it back. Young Max offers to accompany his mom to a wedding but does not know how to dance.
Sydney thinks she is 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.
While out with Mrs. Harris, Sydney gets her ears pierced, which ends up hurting Grandma Judy's feelings. Mom rewrites Young Max's English paper behind his back.
Something embarrassing happens to Sydney while at school, so she holes up in her bedroom. She finds old VHS tapes of Max as a kid, falls asleep and dreams she's in the 90's.
