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.

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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.

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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.

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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.

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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.

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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.

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Jessie hires a new tutor for Luke but it turns out that the tutor has a huge crush on Luke. Meanwhile Ravi downloads an app that predicts the future and fears that Bertram will be endangered.

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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.

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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.

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Ravi begins attending Luke's school.

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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.

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

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Jessie and Zuri read a bedtime story.

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

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Jessie asks another nanny for advice.

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Ms. Chesterfield's shampoo is swapped with glue.

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Jessie doesn't approve of a boy Emma likes.

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Zuri enters the Little Miss Big Apple Pageant.

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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.

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Emma and Zuri hear recreate Jessie's prom on the terrace.

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Zuri refuses to sleep in her room.

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

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

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

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Jessie is in charge of 'Gotcha Day.'

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Ravi notices odd behavior from Mr. Kipling.

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