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 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 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.

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.

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

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 feels torn between spending time with her friends and her fencing teammates. Can she be friends with both groups … or will she have to choose one?

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.

Max is worried when a new smoothie shop creates competition for Reynolds Rides with their new flamingo drink.

With only one month left in seventh grade, Sydney and most of the four amigas are excited, but there's a hiccup when the girls learn that Emmy is failing history and might not pass.

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.

On the Fourth of July weekend, Max surprises Sydney, Olive and Sophia by renting the lake cabin where he spent his best summer in as a kid.

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.

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.

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.

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

Syd finds out her childhood best friend, Harry, is moving back to Portland. When Olive meets Harry, she thinks Harry is the perfect match for Sydney.

Grandma Judy gets to meet her favorite rock star, Davey Rogers.

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.