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.

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.

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.

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.

The Ross kids become concerned that history is repeating itself after a scary old doorman tells them a building legend about a nanny who did “something terrible” to the kids in her care on Halloween. Meanwhile, Jessie and Tony work together to crash an exclusive Halloween party so Jessie can give her short story to a famous magazine editor.

Creepy Connie returns with a sidekick, Mackenzie. The two play a cat and mouse game as they vie for Luke's affection.

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.

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.

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.

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!

Parker and Joey, 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.

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.

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.

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.

When Jessie's dad invites her out to the military camp to visit, Jessie and the kids embark on what should be a pleasant vacation, however when they arrive Jessie is shocked by some news her dad reveals. Not only that Jessie also meets her long time rival Darla again whose younger brother Caleb takes a shine to Emma. Emma and Caleb try to make their relationship work while Jessie and Darla do everything they can to try and break them apart.

When Teddy Duncan (Bridgit Mendler) gets accepted into a college in New York City, she goes to New York, alongside her brother P.J. (Jason Dolley), and meets up with Jessie. When a blizzard traps P.J and Teddy in New York City, Jessie and the Ross kids try to get them back to Denver the rest of the Duncan family go and get them as well. Meanwhile in Colorado, Gabe (Bradley Steven Perry) is being a scrooge.

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.

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.

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.

Jessie and the Ross kids meet Tony's family.

Jessie races to make sure the Ross kids make it to school on time, but there are many bumps along the way.

When Jessie lands two VIP wristbands to Emma and Zuri’s dream concert, the girls compete to be her guest. Meanwhile, Bertram becomes infatuated with his new talking coffee maker.

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.

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.