Jessie Prescott is an 18-year-old teenage girl who moves to New York to live on her own. Once she arrives, she incidentally accepts an offer to become the nanny of a high flying couple's four kids.
After Jessie accepts a date to go on lunch with Tony, Emma gives her dating advice from teen magazines. Ravi becomes the target of Luke's practical jokes.
Jessie comes to the rescue when the condominium board wants Ravi's pet lizard Mr. Kipling out of the building. Zuri brings home another imaginary friend and Luke and Emma compete against each other in a school photo class.
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.
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.
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.
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 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 Zuri go on a train ride. Emma and Ravi get left at the station. Bertram and Luke hunt a spider.
After Zuri's doll is ruined, Zuri and Jessie attempt to raise two hundred dollars for a new one. Meanwhile, Ravi starts as the new kid in the same school with Luke and Emma, but embarrasses Luke after trying to fit in. However, when Ravi defeats the school bully with his traditional Indian Dragon Fire Peppers, everybody praises him, and Luke and Ravi resolve their problems. Jessie helps Emma with a heel problem.
Jessie and Zuri were making a video to send to Jessie's old friend, so Zuri took Christina Ross's tiara so Jessie can wear it. Jessie accidentally knocks the tiara off her head and over the ledge, where it lands in Mrs. Chesterfield's hot tub. When Mrs. Chesterfield refuses to return the tiara, Jessie and Zuri convince Bertram to ask Mrs. Chesterfield on a date so they can take it from her apartment. Meanwhile, Ravi, Emma and Luke all see a video online and have an idea to make Mr. Kipling a star. The title is a send-up of the film title Romancing the Stone.
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.
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 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.
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.
While the Ross Family has their traditional "Gotcha Day", Jessie is left in charge to help celebrate the time when Zuri was first welcomed home in New York City. When Ravi tells the story when he first arrived in the United States, he tells Jessie that they thought Mr. Kipling was supposed to be a baby because his room was decorated as a nursery. Jessie accidently blurts out that Morgan and Christina were probably expecting a baby. Ravi gets incredibly upset; Christina gets infuriated with Jessie. The huge reveal almost ruins "Gotcha Day". Later on, Morgan and Christina tells them that his birth certificate had a typo and instead of Ravi being born in the year 2001, it said 2011, so that is why the Ross' were expecting a baby. In the end, Ravi forgives Morgan and Christina, and they give Zuri a zebra as a "Gotcha Day" present.
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.
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 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.
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.
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 sync. 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 she and Lindsey don't win.
Jessie directs a play she's written and casts Luke as the male lead; the play is a love story, and 'Creepy Connie' is the female lead. Meanwhile, Zuri job-shadows Bertram for her school report.
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.
Mr. Kipling has been acting strangely for some time. He is mean to Ravi and is having wild food cravings. It is revealed that Mr. Kipling is a female lizard guarding her twelve babies, and this startles the entire Ross family. Meanwhile, Zuri is upset when she announces that Millie the Mermaid has died (she accidentally got stabbed by a swordfish). The mailman accidentally ships Mr. Kipling's eggs to a restaurant. Jessie, Ravi, and Luke pretend to be waiters and try to get them back. At the restaurant, the eggs hatch and twelve little lizards are born. The episode ends with the entire family, including Bertram, attending Millie the Mermaid's funeral.
Jessie decides to pursue acting, so she auditions for a TV show.
The Ross kids are scared on Halloween by a legend about an evil nanny who lived in their building. Jessie and Tony crash a Halloween party so Jessie can give her short story to a famous magazine editor.
Jessie joins a comedy improv class and Tony goes to embarrassing lengths to prove his love for her. Ravi recruits Zuri to help him babysit Mrs. Kipling's baby lizards.
Luke takes Kenny the Koala to the first day of school. When it gets loose, Ravi says it's his to cover for Luke and is made fun of. On Emma's first day of high school she meets an interesting new friend, Rosie.
Emma is excited that her mom is planning a fashion show but once Emma sees the terrible designs, she is conflicted about whether she should give an hest opinion.
Ravi mistakenly fears his pet lizards will be made into fashion accessories.
Jessie and the Ross kids meet Tony's family.
Austin needs Jessie's help to get to his gig at Times Square on New Year's Eve!
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 is put in charge of a carnival to raise funds for the school. Meanwhile, Luke watches the carnival from home through binoculars and witnesses a suspicious act.
Zuri is having problems with a teacher at school, so Jessie volunteers in her classroom so she can assess the situation.
Jessie gets her first big acting role in a Shakespeare production in the park, but things go awry when she switches personalities with Zuri.
Zuri trades a cherished toy that Jessie gave her to a collector, but then she tries to get it back. Meanwhile, Luke and Emma attempt to teach Bertram how to dance.
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.
Jessie decides to write Tony a sweet song for their first anniversary, but when he forgets their special day she composes an angry ballad instead that goes viral. Meanwhile, Luke tries to help build Ravi's self-esteem.
Emma gets upset when her friends gravitate to the new girl in school; Ravi helps Luke with a project about India.
Jessie lands a job as a stunt double for a popular Australian actress, but things get tricky when the movie's director and the actress's boyfriend ask Jessie out on a date. Meanwhile, Emma helps sneak Zuri's pet zebra into the penthouse.
Everyone gets trapped in the penthouse panic room after Stuart changes the pass code to be alone with Zuri. Meanwhile, Bertram and Emma help Jessie with an upcoming audition.
Jessie learns that Zuri is a chess prodigy and encourages her to compete in a renowned chess competition. Meanwhile, Luke and Emma suspect that Bertram is a former jewel thief.
Future Jessie appears to warn present-day Jessie that when Ravi grows up he will invent a robot version of Bertram that evolves into an army that tries to destroy Jessie and take over the world.
Jessie loses a pet bunny. Emma gets Luke to help her learn more about sports to impress a guy at school.
Jessie invites Bertram's mom to visit as a surprise on his birthday, much to Bertram's dismay. Meanwhile, Ravi and Luke compete in an egg-drop contest at school.
Jessie offers to help Zuri earn scout badges during a camping trip to Central Park. Luke convinces Ravi that lying is a super power.
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.
Emma and Bryn co-anchor their school's morning announcements; Jessie tricks Zuri into believing that she's an alien after learning that Zuri has been reading her diary.
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.
