Jessie enrolls Luke in a dance class, and to Jessie's dismay, he decides to replace doing homework with dance practice. Meanwhile, Emma and Ravi thinks Zuri have a crush on Tony, and don't know what to do about it.
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.
Connie returns, this time with her boarding school roommate Mackenzie, who appears even crazier than her. When she obsesses over Luke, Connie surprisingly defends him. But things may not be as they seem. Meanwhile, Emma gets fired from her job.
Jessie and Zuri set out to host a birthday party for Taylor, a new friend with 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. Luke, Ravi and Zuri do babysitting behind Jessie's back to earn money.
Jessie and Zuri discover Stuart has a new laid-back "manny" named Hudson. Having grown to like Stuart, Zuri resents being told not to see him, and they run off together. Emma, Luke and Bertram try to help Ravi prepare for a talent show.
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.
Jessie agrees to accompany Bertram to his high school reunion, so he can show his former classmates how successful he has become. Meanwhile, Ravi steals a violent video game to be considered cool, only for his actions to haunt him.
Jessie hits it off with a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield's son. Meanwhile, Ravi and Luke fight about who has the right to a baseball Ravi catches at a Yankees game.
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. Emma and Luke follow Bertram to a renaissance faire.