Jessie and the kids are excluded from the building Halloween party. They throw their own party, which is interrupted when Emma and Luke become possessed by evil spirits.

When Jessie’s dad invites her out to the military camp to visit, Jessie and the kids embark on what should be a pleasant vacation, however when they arrive Jessie is shocked by some news her dad reveals. Not only that Jessie also meets her long time rival Darla again whose younger brother Caleb takes a shine to Emma. Emma and Caleb try to make their relationship work while Jessie and Darla do everything they can to try and break them apart.

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 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.

Future Jessie appears from a time machine to warn present Jessie that Ravi will cause a threat to her future life.

Jessie invites Bertram’s mom out for his birthday. However, Bertram doesn’t like his mom that much because she always steals the spotlight. Now, Jessie needs to bring the two together. Meanwhile, Ravi and Luke work on a science project together.

Luke, Ravi, Zuri, and Stewart get locked in the penthouse panic room.

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.

Emma sneaks out to the school dance to warn Luke that his new crush is going to dump him. Luke gets relationship advice from Adam Sandler. Zuri and Ravi set traps for a burglar.

Jessie loses a pet bunny. Emma gets Luke to help her learn more about sports to impress a guy at school.

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

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.

Emma gets upset when her friends gravitate to the new girl in school; Ravi helps Luke with a project about India.

When Tony forgets their first anniversary, Jessie composes an angry ballad that goes viral. Luke tries to help build Ravi’s self-esteem.

Jessie and the Ross kids meet Tony’s family.

Zuri must get back a cherished toy that Jessie passed on to her after she trades it to a toy collector. Luke and Emma prepare Bertram for a Salsa dancing contest to win his crush’s heart.

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.

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.

Zuri is having problems with a teacher at school, so Jessie volunteers in her classroom so she can assess the situation.

Jessie offers to introduce the kids to NBA All-Star Chris Bosh, who’s in town to play one of Luke’s favorite local basketball teams at the park.

Jessie and the Ross kids meet Tony’s family.

Austin, Ally, Trish and Dez travel to Times Square where Austin is booked to perform on New Year’s Eve. When they can’t get through New York City’s crowded streets, Jessie comes up with a plan to get them to the stage and to ultimately have Austin record one of her songs.

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.

Ravi is having trouble finding a home for all 12 of Mr. 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.

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.

The Ross kids become concerned that history is repeating itself after a scary old doorman tells them a building legend about a nanny who did “something terrible” to the kids in her care on Halloween. Meanwhile, Jessie and Tony work together to crash an exclusive Halloween party so Jessie can give her short story to a famous magazine editor.

Mr. Kipling has been acting strangely for some time. He is mean to Ravi and is having wild food cravings. It is revealed that Mr. Kipling is a female lizard guarding her twelve babies, and this startles the entire Ross family. Meanwhile, Zuri is upset when she announces that Millie the Mermaid has died (she accidentally got stabbed by a swordfish). The mailman accidentally ships Mr. Kipling’s eggs to a restaurant. Jessie, Ravi, and Luke pretend to be waiters and try to get them back. At the restaurant, the eggs hatch and twelve little lizards are born. The episode ends with the entire family, including Bertram, attending Millie the Mermaid’s funeral.

While the Ross Family has their traditional “Gotcha Day”, Jessie is left in charge to help celebrate the time when Zuri was first welcomed home in New York City. When Ravi tells the story when he first arrived in the United States, he tells Jessie that they thought Mr. Kipling was supposed to be a baby because his room was decorated as a nursery. Jessie accidently blurts out that Morgan and Christina were probably expecting a baby. Ravi gets incredibly upset; Christina gets infuriated with Jessie. The huge reveal almost ruins “Gotcha Day”. Later on, Morgan and Christina tells them that his birth certificate had a typo and instead of Ravi being born in the year 2001, it said 2011, so that is why the Ross’ were expecting a baby. In the end, Ravi forgives Morgan and Christina, and they give Zuri a zebra as a “Gotcha Day” present.

Jessie decides to pursue acting, so she auditions for a TV show.

Jessie directs a play she’s written and casts Luke as the male lead; the play is a love story, and ‘Creepy Connie’ is the female lead. Meanwhile, Zuri job-shadows Bertram for her school report.

Jessie, Bertram and the kids head to Bali for a family vacation, but when their private jet starts to experience difficulties, Jessie takes control of the cockpit and makes an emergency landing on a tropical island. Jessie must figure out how to get the kids home safely, all while recovering from poisonous bug bites, escaping scary monsters and tracking down Mr. Kipling.

After the girls watch a scary movie, Jessie tries to help Zuri conquer her fear of dolls by confessing her own fear of porta-potties. Meanwhile, Cameron teaches Ravi how to impress a girl and Bertram listens to opera non-stop to win a radio contest.

Emma and Zuri plan a romantic mystery-filled fifth first date for Jessie and Tony. Meanwhile, Ravi, Cameron and Bertram get stuck in a giant teacup on a billboard, after their failed attempt to rescue Ravi’s toy helicopter.

Nanny Agatha’s twin sister, Angela, is in town and Jessie suspects she is trying to steal her job and also catch Tony’s eye. Meanwhile, Emma copes with a giant zit on her nose.

Zuri enters the Little Miss Big Apple Competition against Lindsey, a kid who Agatha’s watching. But when Jessie finds out that Zuri has no talent,she insists that Zuri lip sing. When Zuri plans to cheat on her schoolwork, Jessie apologizes for teaching her that cheating seems right. Zuri ends up doing an acting scene,but her and Lindsey don’t win.

Jessie has her hands full trying to keep a watchful eye on Emma, who has a major crush on bad boy with a bad reputation, Vincent. Meanwhile, Zuri becomes too protective of her favorite tree in Central Park.

Jessie is tasked with ungluing Mrs. Chesterfield’s hands from her head, while Ravi attempts to uncover who switched Mrs. Chesterfield’s hair gel with stay stick glue. Meanwhile, Tony and Jessie plan a fun date.

Jessie thinks Luke needs strict discipline to keep him from misbehaving and enlists the help of fellow nanny, Samantha, who winds up being a dog nanny. Meanwhile, the kids break into Bertram’s cluttered room and Jessie makes them help clean it up after all of it fell and turned into a huge pile of Bertram’s things which Ravi gets stuck in.

Jessie competes with another nanny named Agatha who forbids her from taking the Ross kids to Central Park. She ends up putting pictures of Jessie online that makes her look like a bad nanny.