Jessie gets worried that Zuri may have imaginary friends her whole life, so she tries to find her an actual friend at the park. Zuri meets Nana Banana, a former clown with a colorful personality, but Zuri begins to favor Nana Banana over Jessie. Jealous, Jessie throws Nana Banana out after a banana peel is left on the stairs, which upsets Zuri. Meanwhile, Mr. Kipling falls in love with a plastic toy animal at the park, so Luke, Emma and Ravi rob it from the park, while trying to avoid Ranger Bill, the park security guard. When they accidentally break the toy and try to return it to the park, they are caught. However, Nana Banana saves them from getting in trouble, which makes Jessie realize her mistake and apologize to Nana Banana, leading to all of them becoming friends.

Future Jessie appears from a time machine to warn present Jessie that Ravi will cause a threat to her future life.

After Jessie embarrasses Luke in front of a bully, he doesn't want her to help him with anything in public. When the mean kid faces off with Luke in the neighborhood paintball contest, Luke has no one to be his partner. Upset, Jessie arrives at the park to prove to Luke that she can help him win the paintball war. Meanwhile, Zuri invites Emma to her tea party, but Emma turns down the invitation when her friend Jasmine gives her a free pass to a fashion show. Zuri invites Bertram instead but doesn't think he's a very good guest during the party, which upsets her. On the day of the fashion show, Jasmine un-invites Emma, so Emma decides to attend her Zuri's tea party to cheer her up. Jessie helps Luke win the paintball competition.

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.

Normally, Jessie reads Zuri a bedtime story, but this time Zuri reads the story, which soon places all of them into a medieval world. Tony will do anything to please one of the princesses, which is Jessie, but there is another guy fighting for her, who is supposed to represent a guy named Brody in the real world. In the real world, a guy named Brody asks Jessie out on a date, which actually causes Tony to become jealous, just like in the medieval story. Both of the boys go on a great medieval "adventure" in the story to try to get Jessie to be their princess. They joust for Jessie, but Tony is obviously weaker than Brody. Besides the medieval storyline, Tony is conflicted about Jessie and Brody going on a date together. In the real world, Jessie finds out Brody also has another girlfriend and decides not to go on a date with him. Tony asks Jessie out on a date and she accepts.

Jessie offers to introduce the kids to NBA All-Star Chris Bosh, who's in town to play one of Luke's favorite local basketball teams at the park.

Jessie thinks Luke needs strict discipline to keep him from misbehaving and enlists the help of fellow nanny, Samantha, who winds up being a dog nanny. Meanwhile, the kids break into Bertram’s cluttered room and Jessie makes them help clean it up after all of it fell and turned into a huge pile of Bertram's things which Ravi gets stuck in.

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.

Jessie loses a pet bunny. Emma gets Luke to help her learn more about sports to impress a guy at school.

Despite being weary of Ravi's seven-foot Asian Water Monitor Lizard, Mr. Kipling, Jessie comes to the lizard's rescue after the head of the condo board attempts to ban Mr. Kipling from the building. Meanwhile, Zuri brings home an another imaginary friend, and Luke and Emma compete against each other in a school photography class.

A celebrity comes to the Ross household. Emma and Jessie fight for his affection,while Zuri and Luke make prank phone calls. The star asks Jessie out but Emma ruins it. Bertram pretends to work while Mr.Ross is in town.

Jessie competes with another nanny named Agatha who forbids her from taking the Ross kids to Central Park. She ends up putting pictures of Jessie online that makes her look like a bad nanny.

Jessie, Bertram and the kids head to Bali for a family vacation, but when their private jet starts to experience difficulties, Jessie takes control of the cockpit and makes an emergency landing on a tropical island. Jessie must figure out how to get the kids home safely, all while recovering from poisonous bug bites, escaping scary monsters and tracking down Mr. Kipling.

Jessie decides to pursue acting, so she auditions for a TV show.

After Jessie and Ravi discover that Zuri is a chess prodigy, Jessie enters Zuri into a chess competition where she can win two tickets for a trip to Paris. Meanwhile, while watching a show about unsolved crimes, Luke and Emma start to believe that Bertram is the "Scuba Bandit" and try to prove this – however, Bertram finds out and forces them to be his crime assistants.In the end, Zuri throws the match so that her opponent can go home to Paris to see his family and make amends, and Luke and Emma discover that Bertram isn't really the Scuba Bandit – he was just pretending to get back at them for believing that he was, but when they're watching the show again, they start to believe that Jessie is the Sweetheart Thief as the episode ends.

Jessie is tasked with ungluing Mrs. Chesterfield's hands from her head, while Ravi attempts to uncover who switched Mrs. Chesterfield's hair gel with stay stick glue. Meanwhile, Tony and Jessie plan a fun date.

Jessie has her hands full trying to keep a watchful eye on Emma, who has a major crush on bad boy with a bad reputation, Vincent. Meanwhile, Zuri becomes too protective of her favorite tree in Central Park.

Emma and Zuri plan a romantic mystery-filled fifth first date for Jessie and Tony. Meanwhile, Ravi, Cameron and Bertram get stuck in a giant teacup on a billboard, after their failed attempt to rescue Ravi's toy helicopter.

Jessie joins a comedy improv class and Tony goes to embarrassing lengths to prove his love for Jessie. Meanwhile, Ravi recruits Zuri to help him babysit Mrs. Kipling's baby lizards.

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.

Zuri is having problems with a teacher at school, so Jessie volunteers in her classroom so she can assess the situation.

When Tony forgets their first anniversary, Jessie composes an angry ballad that goes viral. Luke tries to help build Ravi's self-esteem.

Emma sneaks out to the school dance to warn Luke that his new crush is going to dump him. Luke gets relationship advice from Adam Sandler. Zuri and Ravi set traps for a burglar.

Tony and Jessie attempt to make each other jealous by asking their exes on a double-date, causing the duo to break their dating relationships, which also saddens Emma & Zuri in the process. Meanwhile, Luke & Ravi attempt to sabotage each others' plans on how to relieve Bertram's stress level. Unfortunately, this leads Bertram into thinking that the Ross brothers don't actually care about him. Also, he's hypnotized into thinking that he's a stray tomcat.