In the premiere episode, 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. ...
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 another imaginary friend, and Luke and Emma compete against each other...
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.
Jessie convinces Luke that with her help they can beat the neighborhood paintball rival who wins the game every year. Meanwhile, Zuri plans a tea party, and Emma is invited and promptly uninvited by her best friends to Fashion Week.
After a music producer spots Jessie singing a song she wrote, she is over the moon with excitement about the possibility that her big break has finally arrived. Meanwhile, Bertram enlists Emma to help style him 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 herself in the park and constantly squeaks a yellow horn, Jessie is worried. Meanwhile, Ravi thinks that Mr. Kipling has found true lov...
Jessie believes Connie, a math tutor she finds for Luke, will be the perfect scholarly influence. To Jessie's dismay, Connie turns out to be a lovelorn teen fascinated with Luke. Meanwhile, Ravi is convinced he can predict the future with his Mystery Ball.
When the kids' parents get caught in a snowstorm, Jessie must shop for the kid’s Christmas presents, get the house decorated and take the kids to the mall to see Santa, where they have a run-in with his mischievous elves.
Jessie helps host teen movie star Jordan Taylor who is staying at the Ross' house. As Emma and Jessie vie for Jordan's attention, Zuri, Ravi and Luke rifle through his suitcase and find a few surprises.
Jessie teaches Zuri the value of a dollar when, against the wishes of Mrs. Chesterfield, they set up a lemonade stand in the lobby of their building. Meanwhile, Ravi deals with the trials and tribulations of adjusting to his new American school.
To the kid's dismay, Jessie has everyone take the subway to the cultural fair at Emma's school. Meanwhile, Bertram and Ravi look for a pesky spider that has made its home in the apartment.
After Jessie accidentally drops a diamond tiara belonging to Mrs. Ross onto Mrs. Chesterfield's terrace, Jessie and the kids must think of a creative way to retrieve it when she refuses to give it back. Deciding their best option is Bertram, they convince him to ask Mrs. Chesterfield on a date ...
Fairy tales come alive when Jessie and Zuri read a bedtime story that places the gang in medieval times. Meanwhile, Jessie is excited and Tony is jealous when Brody asks her on date.
Jessie is shunned by New York City's most intimidating nanny. Meanwhile, Bertram teaches Ravi and Luke how to wrestle.
Jessie enlists the help of Samantha, a fellow nanny, after Luke continues to misbehave. However, she later discovers Samantha is actually a dog nanny. Meanwhile, the kids reluctantly agree to help Bertram clean his room.
Jessie is tasked with ungluing Mrs. Chesterfield’s hands from her head, while Ravi attempts to uncover who switched Mrs. Chesterfield's hair gel with stay stick glue. Meanwhile, Tony and Jessie plan a fun date.
Jessie has her hands full trying to keep a watchful eye on Emma, who has a major crush on bad boy Vincent. Meanwhile, Zuri is protective of her favorite tree in Central Park.
After convincing Zuri to enter a pageant, Jesse runs into her nemesis Nanny Agatha, who has entered her beloved Lindsay in the pageant, as well. Meanwhile, Luke and Ravi play practical jokes on Bertram.
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 is bummed about a giant zit she has on her nose.
Emma and Zuri plan a romantic mystery-filled fifth first date for Jessie and Tony. Meanwhile, Ravi, Cameron and Bertram get stuck in a giant teacup on a billboard, after their failed attempt to rescue Ravi’s toy helicopter.
After the girls watch a scary movie, Jessie tries to help Zuri conquer her fear of dolls by confessing her own fear of porta-potties. Meanwhile, Cameron teaches Ravi how to impress a girl and Bertram listens to opera non-stop to win a radio contest.
Jessie, Bertram and the kids head to Bali for a family vacation, but when their private jet starts to experience difficulties, Jessie takes control of the cockpit and makes an emergency landing on a tropical island. Jessie must figure out how to get the kids home safely, all while recovering from...
Jessie writes a play to be produced at the kids' school, but to Luke’s shock, she’s cast Creepy Connie as his love interest. Meanwhile, Zuri job-shadows Bertram for her school report.
Jessie auditions for a role in a television series and is convinced that she can talk her way into getting the part. However, it’s Zuri who impresses the director. Meanwhile Emma, who Jessie left in charge at home, joins Ravi and Luke in search of what they think are carnivorous rats in the walls...
The Ross Family puts Jessie in charge of decorations for a party celebrating the anniversary of Zuri's adoption. Meanwhile, Ravi finds out some surprising news about his own adoption.
After finding a nest of eggs on the terrace, Jessie and Ravi discover that Mr. Kipling is really Ms. Kipling, and a mom-to-be. However, after accidentally misplacing her eggs, Ravi realizes he may have to work at becoming a better grandparent to baby lizards. Meanwhile, Zuri is determined to thro...