When Max has a crush on Sydney's music teacher, Gemma, but realizes he's too nervous about dating again, he convinces Syd to be a chaperone on his first date. In the '90s, Leo has a crush on Max's new math tutor, Danielle. Leo persuades his buddy to need more help so he can see the tutor more. 

When Max hires Sydney to write a jingle for Reynolds Rides, she learns it's not easy to be both a daughter and an employee.