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An idealistic teen from rural Texas embarks on the adventure of a lifetime when she decides to leave behind starry nights for big city lights. Thrilled to be on her own and determined not to be intimidated by New York City, she accepts a job as nanny for a high-profile couple with four kids. Helping to keep her moral compass in check are Bertram, the family's butler, and Tony, the building's 20-year-old doorman.
In the season four premiere, the Ross kids are convinced Jessie is headed to Africa to rekindle her relationship with ex-fiancé, Brooks. In an effort to stop her, the kids make the trip to Africa and quickly find themselves on a wild adventure.
Jessie's stepsister Darla comes to visit, and Jessie enlists Tony's help to try to cover up the fact she didn't go through with the wedding. Meanwhile, Luke shaves for the first time and when Bertram comes to help, things get a bit hairy.
The Ross family faces an unexpected dilemma when they find out their parents have lost all their money and must learn to live without it.
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.
Eager to play in Luke's basketball game, Ravi unexpectedly runs into LA Clippers star Chris Paul, who he enlists to coach him. Meanwhile, Jessie learns that Hudson is her new classmate and is unhappily forced to partner with him for an assignment.
When the kids are snowed in at the penthouse, an epic game of capture the flag ensues. Allegiances are tested, tricks are pulled and everyone goes a little overboard.
In an effort to help Ravi make friends, Jessie takes him to a MENSA meeting in the park. However, their new friends, Madeline and Scott, may be too good to be true.
Emma wants her license, so Jessie teaches her how to drive. Ravi and Luke accidentally break one of Zuri's games, forcing a stand-off.
Bertram has had enough, so decides to quit and to go work for Mrs. Chesterfield. Meanwhile, the Ross family hires a new butler, Roger, who takes his job very seriously.
While on vacation, the Ross family finds a girl stranded in the middle of the ocean and invites her aboard their yacht. Meanwhile, Bertram stays home and babysits Mrs. Kipling, who has separation anxiety from Ravi.
While exploring an Italian island, the Ross family's tour guide tells a story about Jessie's necklace, and how its curse brings anyone who wears it bad luck in love.
In the final part of the "Rossed at Sea" three-parter, Jessie abruptly ends the Ross family vacation because the kids are constantly fighting. They wind up in a pickle when they find the yacht the next morning floating in the middle of the sea with no captain or crew in sight.
It's school dance time, and the Ross family pulls out all of the stops to score dates. Meanwhile, Jessie helps Bertram prepare for his first solo at the Metropolitan Opera.
Bertram's new toupee that he bought for his band's big performance has gone missing, so Jessie interrogates each of the kids in hopes to find it.
When Luke becomes the brain of the family and Zuri the new trendy fashionista, Ravi and Emma feel their identities have been stolen.
When Mrs. Kipling becomes a celebrity, it puts a strain on her relationship with Ravi. Meanwhile, Bertram preps Emma for an audition and Zuri tries to be more independent.
While trick-or-treating, Stuart warns the Ross kids about a ghost named Abigail. Then, at a masquerade party, Jessie meets a mysterious, masked boy who she falls for.
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!
