In a cross-over episode with Joey and Parker Rooney of Liv and Maddie, Jessie and the Ross kids plan a tropical Christmas at the family's vacation villa after Jessie lands a role in the local TV production. While there, Jessie runs into Shaylee Michaels.
Jessie gets an important audition, but her and Ravi end up on the game show "Ride to Riches" in which contestants can win prizes during their taxi ride. Meanwhile Emma and Luke follow Bertram to see what he is up to on his day off.
When Brooks lands a job in Africa and has to be there in two days, he and Jessie are forced to move up their wedding.
The Halloween Festival takes a scary turn when Brooks proposes to Jessie and she learns that none of the Ross kids approve.
Mrs. Chesterfield hires Bertram to find dirt on Jessie that would lead Brooks to break up with her.
Jessie gets to know a new guy she met in the park named Brooks only to later finds out that he is Mrs. Chesterfield's son.
Emma and Zuri compete to attend a Justin Timberlake concert with Jessie, who landed two VIP wristbands to the event. Meanwhile, Bertram becomes infatuated with his new talking coffee maker.
Jessie goes with Bertram to his high school reunion, so he can show his former classmates that he is successful. Meanwhile, Ravi steals a video game after Jessie forbids him to buy it.
Ravi gets a trip to outer space with the rest of the Ross kids and Jessie as a birthday present from his parents, but the journey takes an unexpected turn when Ravi ends up not going.
Jessie recruits the kids to help her make a film in 24 hours, but things get complicated when everyone presents their own ideas about what the movie should be about.
Jessie rushes to get the Ross kids to school on time, but countless obstacles arise.
Stuart has a new 'manny' named Hudson. Jessie thinks the new and cool Stuart is a bad influence around Zuri but when Zuri and Stuart run off together, Jessie and Hudson are forced to work together to find them.
Jessie needs money to buy her dad a birthday gift so she accepts a job at Empire Skate Building before realizing that Emma is her boss.
Jessie connects with a young girl, Taylor, who is a military kid just like her; and Zuri becomes her friend. Jessie then meets Taylor's grandmother who tells her that Taylor's birthday is coming up but her mom is overseas, so Zuri calls in a favor from First Lady Michelle Obama.
Jessie meets a new friend named Abbey in acting class but she discovers that Abbey's not all that she seems.
Creepy Connie returns with a sidekick and the two play a cat-and-mouse game as they vie for Luke's affection.
Jessie notices a famous director in the park and and hooks Zuri up with his daughter, Wendy. But then Zuri discovers that she's a monster. Emma gets a new job after she goes over her phone limit but competition arises when Luke and Ravi open up their own stand and Emma loses her job because they get all the business.moreless
Emma befriends Maybelle, a girl who has just moved into the building, and invites her to Emma's party. Meanwhile, Jessie intervenes with the school music teacher in an effort to allow Ravi and his sitar to join the school band.
Jessie enrolls Luke into a dance class but then he starts to neglect his homework and makes dancing a priority. Meanwhile, Emma and Ravi are determined to find out who Zuri has a crush on.
Jessie meets Teddy Duncan who is heading to New York City to attend college.
Jessie and the kids meet a TV producer named Corinne who offers to make them stars in a reality show.
Luke wants to know more about his birth parents, so he enlists the help of Emma to find out who they are.
Jessie and Tony set up blind dates for each other just to show each other that they are moved on from each other. Ravi lands an internship at the zoo.
Jessie gets the role to be an understudy for a famous Broadway actress and Luke and Ravi conspire to let her play the part. Meanwhile, Bertram enters an online cooking competition.
Jessie's new agent gets her a job as a hand model.
Jessie and the kids throw a Halloween party in which Luke and Emma become possessed.