With her dad’s permission, Sydney enlists Olive to help remodel her bedroom to fit her new “artsy Syd” 8th grade persona. In the ‘90s, Max is struggling being the shortest kid in his class and tries to make himself look taller.

As part of a yearly 8th-grade tradition, Syd and Olive get paired with two 6th graders to mentor. When Sydney sees her mentee Lucy is very shy, she goes a bit overboard trying to help her make friends.

When a storm ruins Olive’s dream bat mitzvah celebration, Sydney helps her figure out a backup plan. In the ’90s, it’s Leo’s birthday, and all he wants is to win a radio contest for passes to meet their favorite rapper, MC Gavel.

When Olive is moved into an advanced math class, Syd pushes to be in the same class but quickly realizes math isn’t really her strongest subject. Back in the ’90s, Max retires his skateboard for roller skates to impress Alisha, but he doesn’t know how to skate.

When Olive learns that her parents are splitting up, Sydney, Max and Grandma Judy come together to lend their support. In the ’90s, Max enlists Alisha to help him plan an elaborate dinner to try and get his parents back together.

Sydney suspects her teacher Ms. Anderson has assigned everyone in her class historical figures to write about based on their race. When Sydney talks to her classmates, they confirm her suspicions and explain how uncomfortable they felt when they received their assignments. The students agree it’s time to stand up for themselves and elect Sydney as their spokesperson to talk to their teacher. In the ’90s, Vice Principal Virmani arranges for a local reporter to interview Leo about his work as founder and president of the school’s computer club, the same club he encouraged his buddy Max and his cousin Alisha to join. Leo provides a great interview and highlights of his work and is excited until the story runs, incorrectly featuring a picture of Max with the title of Club President.

When Max goes away for the weekend and leaves his mother in charge, Sydney takes advantage of her “cool” grandma by arranging a sleepover on a Sunday night. In the ’90s, Judy believes Max broke something even though he keeps denying his involvement.

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.

Sydney is over the moon when her spunky 7-year-old cousin, Lexi, moves in with the Reynolds for the summer.

When Lexi volunteers Syd to sing at church for Youth Day, Sydney starts to wonder if she can pull off singing gospel music. In the ’90s, Max encourages Alisha to perform at open mic night.

When Lexi makes their family’s recipe for their famous sweet potato praline pie, Sydney tries her hand at carrying on the family tradition but misses the mark and her mom.

When Sydney and another congregation member offer to throw the after-church Sunday brunch at the same place and time, a competition ensues