Jessie entrusts her favorite toy from her childhood, Military Mary, to Zuri, but when Zuri trades it for a far less impressive toy, they try desperately to get Military Mary back.
Emma is upset when her friends stand up for the new girl in school. Meanwhile, Luke decides to write a report on India, but makes Ravi do all the work for him.
Jessie wants to prove that she is a great girl scout leader by helping Zuri earn a badge - which proves to be a hard quest. Meanwhile, Ravi's lies puts Bertram in a battle with his arch rival butler.
Jessie loses a bunny that Zuri brings home as a class pet, and she struggles to keep it from Zuri until she finds it. Meanwhile, Emma starts to date a guy who likes sports. Luke is supposed to help her, only to end up "stealing" her date.
Jessie punishes Emma by not letting her go to the school dance. However, Emma still sneaks out to warn Luke about his date's mean and jealous ex-boyfriend. Meanwhile, Ravi and Zuri set up traps all over the penthouse to prevent burglars.
Luke decides that it's time to cut the strings between him and Kenny the koala, with some help from Jessie, but it proves to be quite the challenge. Meanwhile, Stuart comes over to stay for a few days, and reveals a newfound crush on Emma.
Jesse invites Bertram's mom to visit as a surprise for his birthday but Bertram and his mom do not get along; Ravi and Luke compete in a school egg-drop competition.
Jessie is visited by a middle-aged version of herself who arrives from the future to warn her of an army of robot Bertrams invented by Ravi that are seeking to destroy her and take over the world.
Things become tense when Bryn joins the morning announcements and tries to force Emma, Luke and Ravi off the show. Meanwhile, Jessie tries to teach Zuri a lesson after reading her diary.
Jessie becomes suspicious of Tony when he trains a beautiful girl to be the new door-person. Things heat up even more when Jessie's hot ex-boyfriend comes to town. Meanwhile, Luke and Ravi fight on how to best reduce Bertram's stress level.
Jessie and the kids travel to her dad's military base in Texas. While there, she tries to convince her father that she made the right choice by moving to New York, but neither she, the kids nor old family feuds are making it easy for her.
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.
Jessie gets an opportunity to be the understudy in an off-Broadway play. Unbeknownst to her, Luke plots to sabotage the star so Jessie gets to be on stage. Meanwhile, Emma and Zuri help Bertram make a web show in which he is the star.
To prove to Zuri that she's over Tony, Jessie decides that she and Tony will set each other up. Meanwhile, Ravi gets an internship at an animal shelter, and tries to prove worthy of the owner's trust whenever left in charge.
Luke becomes curious about the identities of his biological parents, and starts to investigate with Emma's help after Jessie refuses. However, things don't turn out the way he expected. Meanwhile, Ravi runs for reptile club president.