Jessie accepts a job as a nanny and moves in with the Ross family, high-flying couple Christina, a former supermodel turned business mogul, and Morgan, a famous movie director, their four kids Emma, Ravi, Luke and Zuri and their beloved 7-foot Asian Water Monitor Lizard. Nanny responsibilities are more difficult than Jessie anticipated as she coaches Emma, who is on the brink of a science fair meltdown.

Despite being weary of Ravi's seven-foot Asian Water Monitor Lizard, Mr. Kipling, Jessie comes to the lizard's rescue after the head of the condo board attempts to ban Mr. Kipling from the building. Meanwhile, Zuri brings home an another imaginary friend, and Luke and Emma compete against each other in a school photography class.

After Jessie accepts an invitation for lunch with Tony, the building's doorman, Emma offers Jessie unsolicited dating advice she has learned from her stash of teen magazines. Meanwhile, Ravi becomes the target of Luke's practical jokes.

A celebrity comes to the Ross household. Emma and Jessie fight for his affection,while Zuri and Luke make prank phone calls. The star asks Jessie out but Emma ruins it. Bertram pretends to work while Mr.Ross is in town.

Jessie and Zuri were making a video to send to Jessie's old friend, so Zuri took Christina Ross's tiara so Jessie can wear it. Jessie accidentally knocks the tiara off her head and over the ledge, where it lands in Mrs. Chesterfield's hot tub. When Mrs. Chesterfield refuses to return the tiara, Jessie and Zuri convince Bertram to ask Mrs. Chesterfield on a date so they can take it from her apartment. Meanwhile, Ravi, Emma and Luke all see a video online and have an idea to make Mr. Kipling a star. The title is a send-up of the film title Romancing the Stone.

Normally, Jessie reads Zuri a bedtime story, but this time Zuri reads the story, which soon places all of them into a medieval world. Tony will do anything to please one of the princesses, which is Jessie, but there is another guy fighting for her, who is supposed to represent a guy named Brody in the real world. In the real world, a guy named Brody asks Jessie out on a date, which actually causes Tony to become jealous, just like in the medieval story. Both of the boys go on a great medieval "adventure" in the story to try to get Jessie to be their princess. They joust for Jessie, but Tony is obviously weaker than Brody. Besides the medieval storyline, Tony is conflicted about Jessie and Brody going on a date together. In the real world, Jessie finds out Brody also has another girlfriend and decides not to go on a date with him. Tony asks Jessie out on a date and she accepts.

Jessie thinks Luke needs strict discipline to keep him from misbehaving and enlists the help of fellow nanny, Samantha, who winds up being a dog nanny. Meanwhile, the kids break into Bertram’s cluttered room and Jessie makes them help clean it up after all of it fell and turned into a huge pile of Bertram's things which Ravi gets stuck in.

Nanny Agatha’s twin sister, Angela, is in town and Jessie suspects she is trying to steal her job and also catch Tony’s eye. Meanwhile, Emma copes with a giant zit on her nose.

Ravi is having trouble finding a home for all 12 of Mr. Kipling's baby lizards.

It’s a big night for Jessie and the kids when Emma manages to steal Austin Moon’s shoe during his performance at Times Square on New Year’s Eve and Bertram manages to lose Zuri in the massive crowd. Jessie seizes the opportunity to show Austin and Ally some of the songs she has written.

The Austin & Jessie & Ally All Star New Year crossover starts on Austin & Ally S02E06 Big Dreams & Big Apples (I).

Jessie and the Ross kids meet Tony's family.

Jessie gets her big break as a stunt double to popular Australian actress Shaylee Michaels and the two become fast friends. But chaos ensues when the movie’s director and Shaylee’s boyfriend, MCD , asks Jessie out on a date. Meanwhile, Emma helps sneak Zuri’s pet zebra into the penthouse.

Luke breaks his leg in a dancing accident at the school carnival. Since he is wheelchair-ridden, he stays on the terrace of the penthouse and notices a suspicious figure dressed in black at the carnival. He enlists Emma's help to find out who the shadowy figure is, and it is revealed to be Bertram.

Zuri must get back a cherished toy that Jessie passed on to her after she trades it to a toy collector. Luke and Emma prepare Bertram for a Salsa dancing contest to win his crush's heart.

Jessie and the Ross kids meet Tony's family.

Emma sneaks out to the school dance to warn Luke that his new crush is going to dump him. Luke gets relationship advice from Adam Sandler. Zuri and Ravi set traps for a burglar.

Jessie enrolls Luke in a dance class.

The Halloween Festival takes a scary turn when Brooks proposes to Jessie and she learns that none of the Ross kids approve.

Jessie and the Ross kids plan a tropical Christmas at the family's Hawaiian villa where Jessie reunites with old friend and superstar, Shayelee Michaels.

Jessie goes back to college and ends up in the same class as Ravi. Meanwhile, Zuri brings home a baby giraffe from Africa.

Jessie finds herself in unfamiliar territory when Emma's unexpected behavior gets her into trouble at school. Meanwhile, Luke takes on the role of Sensei to train Zuri for her upcoming karate belt test.

Jessie has to relearn all the "special skills" she listed on her resume for a commercial that she booked. Meanwhile, Ravi convinces Luke that a meteor is headed towards Earth.

When Mom comes home, Jessie heads to L.A. for a role in a movie. But when the kids realize that they still need her, they follow her to Hollywood!