Austin, Ally, Trish, and Dez go to New York City so Austin can perform at Times Square for New Year's Eve but he was no way to go perform. Jessie wants to sing a song with Austin and when they don't like the lyrics that Jessie wrote, they found a lyric that they wrote but it turned out that it was Zuri so Jessie tries to find a way to make sure they don't find out it was Zuri so it wouldn't ruin her chance to sing a song with Austin.
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The Ross kids get concerned after a scary old doorman tells them a chilling story about a nanny that used to live on the 13th floor and how she did "something horrible" to her kids. Luke purposely goes to the 13th floor and strange occurrences that happening. Meanwhile, Jessie and Tony work together to crash an exclusive Halloween party so Jessie can give her short story to a famous magazine editor.
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Jessie writes and directs a play for the school and casts Luke as the main roll. But, Creepy Connie is also cast in the play and tries to become the female lead role and kiss Luke. Zuri job shadows Betram.
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Jessie tries to prove to Emma her new boyfriend is a bad influence. Meanwhile, Zuri tries to save her favorite tree from being torn down.
Jessie tries to prove to Mrs. Chesterfield the kidsaren'tto blame for stealing her hair due and switching it with glue and she alsoattemptsto help her to fix her hair.
Jessie takes advice from a woman who she thinks is a nanny. Meanwhile, Zuri, Ravi and Emma break into Bertram's room to get their confiscated stuff back.
A Nanny creates lies about Jessie and posts them on the internet making Jessie look bad. Jessie becomes tired of this and tries to stop her once and for all.
A famous actor, Jordan Taylor asks Jessie out on a date but starstruck Emma is jealous and does everything she can to make sure Jessie doesn't go on the date. Meanwhile, Luke and Zuri go through Jordan's things.
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It's Christmas time at the Ross house but Mr. and Mrs. Ross must find a different way of getting home after all planes are grounded. Jessie, Emma and Luke are put in mall jail after a run in with a Christmas elf. Meanwhile, Ravi learns about Santa and is terrified of him.
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When Ravi gets sick of Luke and Zuri's pranks, he puts a plan into action to show teach them about Karma. Meanwhile, Jessie gets asked out on a date by Tony but just wants to be friends so things don't get akward between them.
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Jessie doesn't particularly like Mr. Kipling but, A woman in the building has an encounter with him and wants hi out of the building so, Jessie does everything she can to keep Mr. Kipling from being taken away. Meanwhile, Luke and Emma must work together for a Photography class. Also, Zuri is being bullied by an Imaginary friend.
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Jessie Moves to New York after finally moving out of her parents house. After being thrown after her the taxi because she lost her wallet she is confronted by a young girl asking to be her nanny. She accepts and soon learns the job is hectic!
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