After a music producer spots Jessie and Luke performing in the park, he promises them fame and gets them to his studio to shoot a music video. However, Jessie and Luke fight over the spotlight, causing problems. Meanwhile, Bertram enlists Emma to help style him for his social network profile photo, and Zuri and Ravi take Tony's place at the reception desk to prove to Tony that his job is not as hard as he makes it seem. When Tony finds out about Jessie and Luke, he warns them that the "manager" is a fraud who fools people for their money. Jessie and Luke resolve their problems and abandon the manager, and Tony shoots a new music video for Jessie's song with Jessie and all of the children starring in it.

Jessie believes Connie, a math tutor she finds for Luke, will be the perfect scholarly influence, not realizing Connie is obsessed with Luke. Connie asks Luke to a Harry Potter dance, and Jessie forces him to accept. Jessie soon realizes that Connie really is a creepy stalker and tries steering her away from Luke. In turn, Connie steals Luke's beloved stuffed animal, Kenny the Koala, in order to make Luke go to the dance. Once Jessie tells her that Luke has read none of the Harry Potter books, Connie, horrified, declares her love for Luke dead, and leaves. Meanwhile, Ravi is convinced that he can predict the future with his Mystical Eye-ball Application on his tablet.

Jessie and Bertram are left in charge of bringing the Christmas spirit to Ravi, Emma, Luke, and Zuri. Lukes wants to kiss Jessie under the mistletoe. At the toy store, Jessie, Emma & Luke get caught in Toy Jail. But when their parents are stranded because of a blizzard, things go wrong. Zuri tells Ravi about Santa and Ravi gets petrified by him. The parents make it home for Christmas and Luke quickly kisses Jessie.

Zuri enters the Little Miss Big Apple Competition against Lindsey, a kid who Agatha's watching. But when Jessie finds out that Zuri has no talent,she insists that Zuri lip sing. When Zuri plans to cheat on her schoolwork, Jessie apologizes for teaching her that cheating seems right. Zuri ends up doing an acting scene,but her and Lindsey don't win.

After the girls watch a scary movie, Jessie tries to help Zuri conquer her fear of dolls by confessing her own fear of porta-potties. Meanwhile, Cameron teaches Ravi how to impress a girl and Bertram listens to opera non-stop to win a radio contest.

It's the first day of the new school year. Luke brings Kenny the Koala to school, but it falls out of his backpack. Ravi tries to cover for Luke and says that it's his, causing him to be made fun of. Meanwhile, it's Emma's first day of high school and she meets an interesting new friend, Rosie.

Christina is having a fashion show and is worried that the owner of a fashion blog, Tippi Trashbot, will give her show a bad review.

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.

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.