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.
Jessie goes back to college and ends up in the same class as Ravi. Meanwhile, Zuri brings home a baby giraffe from Africa, and Emma pranks Luke so he thinks he is going crazy.
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.
Ravi wants to play on Luke's basketball team, but he is not great at sports. Jessie has an assignment on diplomatic resolutions, which comes in handy when Zuri and Emma fall out.
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.
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.
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.
When Luke becomes the brain of the family and Zuri the new trendy fashions, Ravi and Emma feel their identities have been stolen. Meanwhile, Bertram wonders what might be behind the only door in the penthouse he hasn't opened.
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.
When Jessie makes the Ross kids bring Stuart along for trick-or-treat he tells them a haunting story about Abigail, a ghost who is out to get them. One by one, the kids mysteriously disappear.
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.
In the series finale, when Christina Ross returns home, Jessie heads to L.A. for a role in a movie. But when the kids realize that they still need her, they follow Jessie to Hollywood.