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

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.

Luke asks his adoptive mom, Christina, for information about his family history after he is assigned a report at school.

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

Jessie hits it off with a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield's son.

Jessie and the kids are excluded from the building Halloween party. They throw their own party, which is interrupted when Emma and Luke become possessed by evil spirits.

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.

Jessie is excited when she and the Ross kids are invited to participate in a reality show.

Jessie enrolls Luke in a dance class.

Jessie makes a friend in acting class only to find out her new pal Abbey is not all that she seems.

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 is on a mission to get to an important audition; however, she and Ravi wind up on the "Rides to Riches" game show in which contestants can win prizes during their taxi ride.

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.

Jessie decides that she and Tony will set each other up.

Jessie and Zuri set out to host a birthday party for Taylor, a new friend who’s sorely missing her mother, a deployed member of the military. When Taylor decides she’d rather not celebrate anything without her mother, Zuri enlists the help of Mrs. Obama.

Jessie is in need of some extra money to buy a special gift for her dad's birthday. She accepts a job at Empire Skate Building only to find out that Emma is her boss.

Unhappy with her son's budding relationship, Mrs. Chesterfield hires Bertram; she's hoping he finds dirt that will cause Brooks to break up with Jessie.

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

Jessie and Zuri discover Stewart has a new laid-back "manny" named Hudson. Having grown to like Stewart, Zuri resents being told not to see him, and they run off together.

Jessie agrees to accompany Bertram to his high school reunion, so he can show his former classmates how successful he has become.

Jessie gets an opportunity to be the understudy in an off-Broadway play. Unbeknownst to her, Luke plots to sabotage the star so Jessie gets to be on stage. Meanwhile, Emma and Zuri help Bertram make a web show in which he is the star.

Jessie asks Emma to invite the new girl from the building to her party as a welcoming gesture.

Jessie hooks Zuri up with a new girl named Wendy McMillan after seeing a director to get her acting career started. With Jessie she's an angel, but while Bertram is in charge, she tears up the place and wrecks everything. Bertram tries to take care of it, but Wendy hooks Bertram up too. Zuri tells Jessie she's a monster and wants to stop playing with her. Meanwhile, Emma goes over her limit on her cell phone bill, so Jessie forces her to get a job so she can pay the bill herself.

Jessie becomes frustrated that she can't land any acting gigs, so she takes matters into her own hands by participating in a 24-hour film festival. She recruits the kids to help her direct, shoot and edit her film, but things get complicated when all the kids have their own ideas about what the film should be.

Ravi's birthday present from his parents is a trip to outer space with the rest of the Ross kids and Jessie. Their trip takes an unexpected turn when Ravi ends up not going.