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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; she later finds out that he is Ms. Chesterfield's son.
Stuart has a new 'manny' named Hudson; Jessie thinks the new and cool Stuart is a bad influence around Zuri so Zuri and Stuart run off together leaving Jessie and Hudson having to work together to find them.
Jessie needs money to buy her dad a birthday gift. She accepts a job at Empire Skate Building before realizing that Emma is her boss.
Jessie connects with a new young girl after she's 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 Mrs. Obama and gets her to fly Taylor's mother home for her 10th birthday.moreless
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 the girl from dog of a blog and ant farm.
Jessie notices a 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 a new girl named Maybelle, who has moved into the building and invites her to her party.
Jessie enrolls Luke into a dance class but then he starts to neglect his his responsibilities 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 Corrine who offers them a TV show, and they are all excited.
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.
Jessie auditions and gets the role to be an understudy for a famous Broadway actress, but she wants to play the role herself.
Jessie and the kids throw a Halloween party in which Luke and Emma become possessed.