The second season begins with Jessie trying to crash an exclusive Halloween party so she can give a short story she wrote to a famous magazine editor. Meanwhile, the Ross kids become frightened after a doorman tells them a scary story about a nanny.

Jessie joins a comedy improv class and Tony goes to embarrassing lengths to prove his love for Jessie. Meanwhile, Ravi recruits Zuri to help him babysit Mrs. Kipling's baby lizards.

It's the first day of the new school year. Luke brings Kenny the Koala to school, but it falls out of his backpack. Ravi tries to cover for Luke and says that it's his, causing him to be made fun of. Meanwhile, it's Emma's first day of high school and she meets an interesting new friend, Rosie.

Ravi is having trouble finding a home for all 12 of Mr. Kipling's baby lizards.

Christina is having a fashion show and is worried that the owner of a fashion blog, Tippi Trashbot, will give her show a bad review.

Austin, Ally, Trish, and Dez go to New York to perform at Times Square for New Year's Eve but no way to get in. Jessie wants to sing a song with Austin but it turned out that the good lyrics came from Zuri but Jessie doesn't want anyone to know that it's her.

Jessie is worried Tony is planning on proposing to her after he invites her out for a special evening to meet his parents, so she drags Zuri and her new friend Stuart to the dinner to keep him from doing anything romantic. Tony also puts a tracking app on Jessie's phone and buys Jessie and him a bathroom to live in. Meanwhile, Stuart develops a crush on Zuri and she doesn't appreciate it.

Jessie introduces the kids to an NBA All Star Chris Bosh who is going to be playing the Knicks. So that the New York Knicks can win, Luke washes out the luck of Chris's socks so he loses. Then he realizes that Chris Bosh starts to lose his memory and to lose his skills in basketball. Meanwhile, a famous fashion designer sends Emma a dress to review on her fashion blog. However, things get complicated when Jessie accidentally damages the dress when Ravi and Luke spill a bucket of water all over Emma's new dress.

Jessie volunteers to help out in Zuri's classroom; Ravi learns that Mr. Kipling is actually Mrs. Kipling.

Jessie gets her big break as a stunt double to popular Australian actress Shaylee Michaels and the two become fast friends. But chaos ensues when the movie's director and Shaylee's boyfriend, MCD , asks Jessie out on a date. Meanwhile, Emma helps sneak Zuri's pet zebra into the penthouse.

Luke breaks his leg in a dancing accident at the school carnival. Since he is wheelchair-ridden, he stays on the terrace of the penthouse and notices a suspicious figure dressed in black at the carnival. He enlists Emma's help to find out who the shadowy figure is, and it is revealed to be Bertram.

Zuri trades a cherished toy that Jessie gave her to a collector, but then she tries to get it back. Meanwhile, Luke and Emma attempt to teach Bertram how to dance.

Things get complicated after Jessie and Zuri switch personalities just when Jessie has her first big acting part.

Jessie and Tony's first anniversary is coming up and Jessie wants him to write a song in which she expresses how much he means to her. But when she thinks he has forgotten it, she writes an angry song that is known about Emma's video blog rapidly. The surprising success could be Jessie's breakthrough, but what about Tony? Ravi has consistently poor grades in physical education. Therefore it Luke, who is very good at sports can win in a competition to build his confidence. But Ravi has gained a little too much self-confidence.

Emma is upset when her friends stand her up for the new girl in school. Meanwhile, Luke has Ravi help him with his project about India for their school's multicultural night.

After Jessie and Ravi discover that Zuri is a chess prodigy, Jessie enters Zuri into a chess competition where she can win two tickets for a trip to Paris. Meanwhile, while watching a show about unsolved crimes, Luke and Emma start to believe that Bertram is the "Scuba Bandit" and try to prove this – however, Bertram finds out and forces them to be his crime assistants.In the end, Zuri throws the match so that her opponent can go home to Paris to see his family and make amends, and Luke and Emma discover that Bertram isn't really the Scuba Bandit – he was just pretending to get back at them for believing that he was, but when they're watching the show again, they start to believe that Jessie is the Sweetheart Thief as the episode ends.

At a slumber party, Luke calls Jessie to pick him up because he misses Kenny, With Jessie's guidance Luke decides that it's time to give up Kenny his stuffed koala, so he tries to spend one night without Kenny and gives him to Jessie to take care of. He was probably able to make it but when Jessie tried to give it back to Luke she ended up dropping him into traffic therefore cutting his arm and head off off but Stewart thinks he can fix Kenny by performing emergency surgery.

Jessie offers to help Zuri earn scout badges during a camping trip to Central Park. Luke convinces Ravi that lying is a super power.

Emma falls for a cute boy named Brett Summers till Luke takes advantage of him. Meanwhile, Jessie loses Zuri's pet bunny, which Bertram is extremely scared of. In the end, Zuri's class bunny has babies.

Jessie grounds Emma, telling her she can't go to the school dance, so she sneaks out to warn Luke that his new crush's ex-boyfriend is going to embarrass him. At the dance, Adam Sandler gives Luke some relationship advice. Meanwhile, Zuri and Ravi set traps to catch a burglar. In the end, Jessie comforts Luke and ends up dancing with him at the school dance.

Everyone gets trapped in the penthouse panic room after Stuart changes the pass code to get alone time with Zuri. Meanwhile, Bertram and Emma help Jessie with an upcoming audition.

Jessie invites Bertram's mom to visit as a surprise for his birthday. However, unbeknownst to Jessie, Bertram and his mom do not get along. Meanwhile, Ravi and Luke compete in a school egg-drop competition.

Future Jessie appears from an elevator time machine to warn present Jessie to run for her life. She tells Jessie that when Ravi grows up, he invents a robot version of Bertram (a "Bertram-Bot") that evolves into an army which tries to destroy Jessie and take over the world.

Jessie post a secret and Zuri reads it and thinks that Jessie is an alien, but Zuri tries to make Jessie to think that she's and alien too.

Tony and Jessie attempt to make each other jealous by asking their exes on a double-date, causing the duo to break their dating relationships, which also saddens Emma & Zuri in the process. Meanwhile, Luke & Ravi attempt to sabotage each others' plans on how to relieve Bertram's stress level. Unfortunately, this leads Bertram into thinking that the Ross brothers don't actually care about him. Also, he's hypnotized into thinking that he's a stray tomcat.

Jessie goes with the kids to the military base where her father lives and discovers that her father is about to be married to the mother of Jessie's high school rival.