1.38: Jessie must work on a project with an eager Hudson, much to her dismay. Elsewhere, Emma tries to sneak out to go to a party without Jessie knowing and Bertram and Zuri watch a marathon of their favorite show in order to find out a secret in the series finale. Her actions lead her to star in a new television show about a superhero nanny. Ravi is so heartbroken without his pet that he decides to stay on the island until Mr. Kipling returns to him. After a few misunderstandings, Jessie and the children are convinced that Ms. Chesterfield is turning the lizards into accessories, so they embark on a journey to rescue the lizards.
Meanwhile, Emma's new rebellious and temperamental behavior becomes a big impact on her and Jessie. After Agatha refuses to let her stay in her apartment, Jessie tells her she can stay at the Ross household. Jessie grounds Emma after she neglects to pick up Zuri from school and accidentally reveals it, telling her she cannot go to the school dance. Connie returns shortly after Luke meets a girl named Mackenzie. Now, they must set out and save Mrs. Kipling from the maniacal zoo caretaker Ms. Lumpkey. 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 Rosses were expecting a baby. Jessie meets Bertram, a sarcastic, lazy butler, and adoptive parents, Morgan and Christina Ross. Emma pleads Bertram to look inside of himself and say that he can do it. Random bullies witness the incident and laugh at him. Meanwhile, Bertram tries to work hard to get a week off.Jessie and the Ross kids struggle to navigate the New York City Subway system, while the grounded Luke teams up with Bertram to defeat a spider.Jessie and Zuri sneak into Mrs. Chesterfield's apartment.Jessie is bullied by a bossy nanny and ends up on her website.Nanny Agatha's twin sister Angela arrives from England, and seems to be the opposite of everything Agatha is, until Jessie begins to suspect that the girl is trying to steal the kids and Tony from her. Then they play a game and then he leaves and tells her that he is studying. In the end, Ravi forgives Morgan and Christina for the mishap and they give Zuri a zebra as a "Gotcha Day" present. Jessie does not know if she should marry Brooks, so she says she needs time to think. Meanwhile, Luke and Zuri raise money to have Jessie "babysit" for children. Meanwhile, Zuri is upset when she announces that Millie the Mermaid has died (she got stabbed by a Rumors arise of a man named Grimm Holloran, a doorman with a strange personality. Meanwhile, at the penthouse, Bertram is sick and tired of Luke and Ravi constantly "nurpling" each other, so he teaches them a lesson by teaching them how to wrestle. Roger then walks in and Mrs. Rhoda Chesterfield hires him to be her new butler. Later, she takes Emma to the Luke and the girls pull a prank on Bertram, but it makes Bertram reach his wits, quit his job, and work for Mrs. Rhoda Chesterfield. MK Digital. Jessie notices that Emma is constantly doing her homework at the last minute; now she is doing the same for her While shooting a video to show to one of her friends back in Texas, Jessie puts on an expensive Normally, Jessie reads Zuri a bedtime story, but this time Zuri tells the story to Jessie, which soon places all of them into a medieval world. Jessie and the children take a vacation on the Ross' yacht for their one-month vacation. They hire her to be the nanny to Zuri, Ravi, Luke, who gets a crush on Jessie, and Emma.
Emma tries to help Maybelle become a New Yorker, but it does not seem to work. However, he cannot do it and does cup stacking at the show instead and wins the first-prize trophy. Kenny the Koala has always been there for Luke during countless days and nights, until one day when his obsession crosses the line. To avoid being mocked by Darla for not going through with her wedding to Brooks, Jessie lies and tells Darla that Tony is Brooks. (Bring Your Own Boa) tea party, but Emma turns down the invitation when her friend Jasmine gives her a free pass to a fashion show. Christina books an acting gig for Jessie in an attempt to spend more time with the children. Zuri brings home another imaginary friend and Luke and Emma work together in a school photo class project.After Jessie accepts a date to go on lunch with Tony, Emma gives her dating advice from teen magazines.