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

Sydney enters a songwriting contest for a pop singer, and finds out the producers at his record company want to drastically change her song.

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.

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 her friends make a pact to go to the dance together without dates. Max recalls his first school dance when Leo and his Mom gave him tips on how to ask a girl to be his date.

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.

Syd returns home from music camp feeling more mature and independent.

How the Syd Stole Christmas was the 1st episode of season 2 of Sydney to the Max. In the present day of the episode, Sydney who is played by (Ruth Righi) rediscovers her love for Christmas after her mother passed away. in the past day, Max who is portrayed by (Jackson Dollinger) decided to take his early Christmas present to school. It was all fun and showing off, until Pete, who is played by (Arjun Sriram) decided to steal the jacket.

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.

Max is fed up with Sydney missing her curfew multiple times and grounds her right before the one-night-only Pop-Up cake museum that all of her friends are attending.

When Sydney and Olive accidentally destroy a very popular exhibit at the museum, their teacher Mrs. Harris is deemed at fault and in jeopardy of losing her job. The girls devise a plan to convince VP Virmani not to fire Mrs. Harris.

Sydney is excited when she makes the school's first girls fencing team. But when she learns her dad helped Coach Carlock, Sydney fears she may have gotten on the team for the wrong reason.

Sydney gets her first period, and when she has an accident at school, she's too upset and wants to sit out her bass solo at the school concert.

Sydney decides to post one of her songs online to expand her audience.

Harry is moving back to Portland and Sydney struggles with the idea of a long distance relationship.

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

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.

A middle schooler and her protective single father learn they have more in common than they realize.

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

Sydney is turning 13 and sets out to plan a sophisticated birthday party. Her plans remind Max of when he tried to organize his own surprise party for his thirteenth birthday back in the 90s.

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.

Sydney is ecstatic when Max leaves town and her Grandma Judy is left in charge.

Sydney and her friends are excited about Halloween and their peanut butter and jelly group costume until they discover they are the only eighth-graders in costumes at school.

In trying to help Olive stand up to her brothers, Sydney learns sibling dynamics are more complicated than she thought.

A middle schooler and her protective single father learn they have more in common than they realize.

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 hosts a slumber party with all of her friends, but the night takes a turn when a group selfie sparks a fight among Emmy and Sophia, and they must help them reconcile.

Max is excited to be honored with The Heart of Portland award for his philanthropic work. But things go awry when Max's dad, who he's not on the best terms with, comes to visit.

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.

On the last day of school, Syd reads through all the notes in her yearbook, and notices an anonymous note from someone confessing that they have a crush on her.

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 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.

Syd, Olive, Sophia, and Emmy are excited that their design for the float honoring brave women was chosen for the annual Portland Parade, but she must come to grips when the girls and their mothers begin to disagree with each other.

A middle schooler and her protective single father learn they have more in common than they realize.

Max, Syd and Grandma Judy talk with Olive about how they've coped with divorce in their family.

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.

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 really wants to attend a Rock 'n Roll summer camp but doesn't know how to tell her dad, especially since he just started a songwriter's night at the shop's café so she could work on her music.