Jessie Prescott is an 18-year-old teenage girl who moves to New York to live on her own. Once she arrives, she incidentally accepts an offer to become the nanny of a high flying couple's four kids.

Jessie comes to the rescue when the condominium owner wants Ravi's pet lizard Mr. Kipling out of the building. 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. Ravi becomes the target of Luke's practical jokes.

Jessie teams up with Luke to beat the paintball rival who wins every year. Meanwhile, Zuri plans a tea party and Emma is invited and promptly uninvited by her best friends to Fashion Week.

Jessie gets her big break when a music producer spots her singing a song she wrote. Emma helps Bertram look good for his social network profile photo.

Jessie wants Zuri to play with real friends instead of imaginary ones, but when Zuri befriends the much older Nana Bananas - who wears yellow track suits, talks to her late husband named Harold in the park, and constantly squeaks a yellow horn when she makes jokes, Jessie is worried. Meanwhile, Ravi thinks that Mr. Kipling has found true love with a playground dinosaur. Written by Medianet

Jessie encounters a girl named Connie who has a crush on Luke. She decides to hire her to tutor Luke. When Luke declines Connie's invitation to a dance, things get violent, and everyone sees why they call her Creepy Connie. Meanwhile, Ravi purchases an app that tells the future, and he and Zuri think that Bertram is in danger.

When Morgan and Christina get stuck in a snowstorm, the family fears they won't make it home in time for Christmas and Jessie is left with shopping for the kid's Christmas presents. When Jessie takes the kids to the mall to see Santa, they have a run-in with his mischievous elves. Written by Disney

Morgan has decided to put Jordan Taylor in his next movie but Jordan will only do it if no one knows that Jordan is at their house and if the family respects him. It causes chaos when Emma gets jealous when Jordan asks Jessie out then tells the whole world about it, Ravi tries to prove about acting to Jordan, and Luke and Zuri keeps prank calling the people in Jordan's phone. Meanwhile, Bertram tries to work hard to get a week off. Written by Joshua Shin

Ravi begins attending Luke's school.

Jessie takes the kids out to go to all the places they need: Emma needs to go to the zoo for her project of monkeys, Ravi needs to see some New York sights, and Zuri needs a playground to play at. However, they get hopelessly lost In the subways. Luke stays at home with Bertram and they attempt to kill a deadly spider, until it gets eaten by Mrs. Kipling.

Jessie and Zuri sneak into Mrs. Chesterfield's apartment.

Jessie meets a handsome man, whom she starts dating, much to the chagrin of Tony. He is rich; however, Zuri discovers that he is cheating on Jessie. She tells Jessie a bedtime story involving them all. It goes like this (basically): Jessie is a princess with her maid (Emma), watching a joust. Everyone is listening to the jester (Bertram) and waiting for the prince (Jessie's new boyfriend) to joust (along with his assistant Luke) . An inventive peasant (Tony) loves Jessie and goes to a sorcerer (Ravi) and his assistant (Zuri) to get a potion. Ravi says to joust vs. the prince. He does and even though he loses, he saves everyone from a dragon (Mrs. Kipling). Then Jessie hears the boyfriend talking on the phone to another girl, so she dumps him and flirts a little with Tony.

Jessie is bullied by a bossy nanny and ends up on her website.

Jessie asks another nanny for advice.

Someone switches Mrs. Chesterfields shampoo with glue. She blames the Rosses because they had all ridden together in an elevator recently. Ravi interrogates everyone: Zuri has paper glued all over her hands, but it's only because she did origami. Emma glued her hand to her phone, but it's because she broke it and fixed it. Luke used it to glue Bulls eyes to Bertram's butt. Bertram used it to glue the trophy he broke back together. Finally, they find mrs. Chesterfields shampoo in jessies purse. To prove herself innocent, she looks at the security camera and finds that mrs chesterfields dog switched them. Jessie skips her date to help chesterfield get the glue out but succeeds in getting glued to her and ripping out her hair.

Emma likes a bad boy, and Jessie does not approve of her seeing him. Emma rebels and sees him anyway. Jessie worries that Emma will get hurt like she did years ago. Emma throws a party, and her and Jessie talk about boys and have a bonding moment.

Zuri enters the Little Miss Big Apple Pageant.

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. Elsewhere, Emma is horrified to find a massive pimple on her nose. Written by Daniel Timothy Dey

Jessie and Tony have their fourth first date on the Rosses terrace, which Emma and Zuri recreate to look like Jessie's senior prom. However, things go badly when Luke, Ravi, and Bertram are all trapped in a giant teacup advertisement, so Jessie and Tony have to save them.

Zuri refuses to sleep in her room.

Jessie and the kids fly off to meet the parents in a private jet.

Jessie directs a play she's written at the kids' school.

Jessie decides she wants to try acting and plans on auditioning for a show.

Jessie is in charge of 'Gotcha Day.'

Ravi notices odd behavior from Mr. Kipling.