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26 Episodes 2011 - 2012
Episode 1
Fri, Sep 30, 201124 mins
Jessie Prescott arrives in New York City, where she is dumped out of her cab at the Ross' luxury condo building (Fairfield) and meets a little girl named Zuri and the doorman of the Fairfield, Tony. Witnessing her nanny Kate running out hysterically, Zuri asks Jessie to be her new nanny. Refusing, Jessie passionately states that she came to New York to follow her dream. Taking it as a joke, Zuri kindly pulls Jessie upstairs, saying how she likes her food. Jessie meets Bertram, a sarcastic, lazy butler, and adoptive parents, Morgan and Christina Ross. They hire her to be the nanny to Zuri, Ravi, Luke, who gets a crush on Jessie, and Emma. After initially failing to win over each child, they attempt to run away. She soon makes up her mistakes to each child except Emma, who is upset that her parents cannot attend her science fair. Jessie flies the Ross' helicopter to the movie set in Chicago where Morgan and Christina are telling them that they need to spend more time with their children, as their presence is important in their lives; this move gets her fired. Nevertheless, she attends Emma's science fair to support her. However, Emma's parents show up to the science fair as well, having taken Jessie's advice. In the end, Emma wins the science fair and Jessie is rehired. Each child attempts to give Jessie another chance. Guest stars: Christina Moore as Christina Ross, Chris Galya as Tony, Brian Carpenter as Head Judge and Bryan Oakes Fuller as A.D., Charles Esten as Morgan Ross.

Episode 2
Fri, Oct 7, 201123 mins
When Mr. Kipling suddenly escapes into Mrs. Chesterfield's apartment, Jessie and Ravi attempt to bring him back and convince Mrs. Chesterfield to let Ravi keep his lizard. Meanwhile, Emma and Luke are assigned as partners for a photography project in their school (Walden Academy), but they argue over who does what task. When Luke takes an awesome photo of a hawk on Grand Central, he gets a lot of credit even though he did nothing toward the report. Elsewhere, Zuri gets bullied by one of her imaginary enemies, Genevieve. Guest stars: Chris Galya as Tony, Carolyn Hennesy as Mrs. Chesterfield.

Episode 3
Fri, Oct 14, 201123 mins
After Jessie accepts an invitation for lunch with Tony, Emma offers Jessie unsolicited love advice she read from her favorite teen magazine. Meanwhile, Ravi gets sick of being the target of Luke's practical jokes, so he decides to get back at Luke by telling him that his karma will get him. Guest star: Chris Galya as Tony.

Episode 4
Fri, Oct 21, 201123 mins
After Jessie embarrasses Luke in front of a bully, he does not want her to help him with anything in public. When the mean child 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 contest. Meanwhile, Zuri invites Emma to her B.Y.O.B. (Bring Your Own Boa) tea party, but Emma turns down the invitation when her friend Jasmine gives her a free pass to a fashion show. However, when Emma is ready for the fashion show, Jasmine gives the passes to the Olsen Twins, so Bertram insists that Emma spends the day with Zuri after he had been the unwanted guest at the tea party for the last part of the episode. Guest stars: Ava Penner as Jasmine Epstein, Devan Leos as Trevor.

Episode 5
Fri, Oct 28, 201123 mins
Jessie practices her guitar skills and plays in Central Park. People notice her and give her money. While she plays, Luke hip-hops and they find out that they earn more money that way. After J.J. Mayfield, a music producer, spots Luke and Jessie performing in the park, he promises them fame and gets them to his studio to shoot a music video. However, Jessie and Luke have to pay $1,200 in order to make the music video and produce it. During the shooting of the music video, they fight over the spotlight, causing problems. Meanwhile, Bertram enlists Emma to help "style" him for his social network profile photo, but things get out of hand when Bertram finds out he can edit his photo to look thinner. Bertram only signed up for the social messaging site to meet an old high school crush. In the end, it turns out that she had around four children and wanted to have more. Meanwhile, 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, but after throwing up in someone's grocery bag and dealing with cookie peddlers, they decide that maybe it was too much for the two of them to handle. Guest stars: Chris Galya as Tony, Arvie Lowe Jr. as J.J. Mayfield.

Episode 6
Fri, Nov 4, 201123 mins
Jessie wants Zuri to play with real friends instead of imaginary ones, but when Zuri befriends the much older Nana Bananas - who wears yellow track suits, talks to her late husband named Harold in the park, and constantly squeaks a yellow horn when she makes jokes, Jessie is worried.

Episode 7
Fri, Nov 18, 201124 mins
Jessie encounters a girl named Connie who has a crush on Luke. She decides to hire her to tutor Luke. When Luke declines Connie's invitation to a dance, things get violent, and everyone sees why they call her Creepy Connie. Meanwhile, Ravi purchases an app that tells the future, and he and Zuri think that Bertram is in danger.
Episode 8
Fri, Dec 9, 201123 mins
When Morgan and Christina get stuck in a snowstorm, the family fears they won't make it home in time for Christmas and Jessie is left with shopping for the kid's Christmas presents. When Jessie takes the kids to the mall to see Santa, they have a run-in with his mischievous elves.

Episode 9
Fri, Jan 6, 201223 mins
Morgan has decided to put Jordan Taylor in his next movie but Jordan will only do it if no one knows that Jordan is at their house and if the family respects him. It causes chaos when Emma gets jealous when Jordan asks Jessie out then tells the whole world about it, Ravi tries to prove about acting to Jordan, and Luke and Zuri keeps prank calling the people in Jordan's phone. Meanwhile, Bertram tries to work hard to get a week off.

Episode 10
Fri, Jan 20, 201223 mins
Ravi finally starts his first day of school with Emma and Luke. Ravi's first day doesn't go well when he accidentally embarrasses his brother and he ends up angering a bully. Meanwhile, Jessie teaches Zuri how to earn money so she can buy a doll by opening a lemonade stand, this proves to be difficult for them. Emma purchases a pair of high heels, but she begins to have a difficult time walking in them.

Episode 11
Fri, Jan 27, 201223 mins
Jessie takes the kids out to go to all the places they need: Emma needs to go to the zoo for her project of monkeys, Ravi needs to see some New York sights, and Zuri needs a playground to play at. However, they get hopelessly lost In the subways. Luke stays at home with Bertram and they attempt to kill a spider.

Episode 12
Fri, Feb 10, 201223 mins
When Jessie wears one of Christina's crowns in order to prove to Jessie's enemy Darla that she is 'rich', she drops the crown over the terrace and into Mrs. Chesterfield's hot tub, so Jessie and Zuri have to sneak into Mrs. Chesterfield's apartment to get it back, and they enlist Bertram to distract Mrs. Chesterfield by asking her to a 'date'. Meanwhile, Emma, Ravi, and Luke try to make Mr. Kipling do stunts.

Episode 13
Fri, Feb 24, 201223 mins
Jessie meets a handsome man, whom she starts dating, much to the chagrin of Tony. He is rich; however, Zuri discovers that he is cheating on Jessie. She tells Jessie a bedtime story involving them all. It goes like this (basically): Jessie is a princess with her maid (Emma), watching a joust. Everyone is listening to the jester (Bertram) and waiting for the prince (Jessie's new boyfriend) to joust (along with his assistant Luke) . An inventive peasant (Tony) loves Jessie and goes to a sorcerer (Ravi) and his assistant (Zuri) to get a potion. Ravi says to joust vs. the prince. He does and even though he loses, he saves everyone from a dragon (Mrs. Kipling). Then Jessie hears the boyfriend talking on the phone to another girl, so she dumps him and flirts a little with Tony.

Episode 14
Fri, Mar 9, 201223 mins
A bossy nanny named Agatha and a snobby kid named Axel starts bullying Jessie and Zuri, respectively. Agatha bans Jessie and Zuri from setting foot in Central Park; leading to Jessie and Zuri to take a stand against Agatha and Axel. Fiona reveals to Jessie that Agatha takes inaccurate photos and she posts them on the internet to make the person look like they are unfit of taking care of a child. At the penthouse, Jessie and Zuri see the photos that Agatha has posted on her blog. Jessie and Zuri try to delete the e-mail that Christina has got from Agatha, the two reveal to Christina that the photos were taken out of context. Christina believes Jessie and she agrees to help her stop Agatha. Jessie, Zuri, and Christina go to Central Park to confront Agatha, but she refuses to apologize, causing Christina to blackmail Agatha for her ungrateful actions. Agatha finally gives in and she promises to apologize for posting inaccurate photos. Meanwhile, Luke and Ravi's sibling rivalry starts to get on Bertram's nerves and he gets the brothers to resolve their differences by wrestling. Unfortunately, Luke and Ravi become exhausted from the training and the lack of sleep. Christina praises Bertram for stopping Luke and Ravi's bickering.

Episode 15
Fri, Mar 30, 201223 mins
Jessie has been trying to figure out a way to discipline Luke, after he gets in trouble at school. Jessie begins taking advice from a nanny on how to discipline Luke, it leads to unusual consequences, when Luke starts behaving like a dog. Emma, Ravi, and Zuri have become fed up with Bertram confiscating their possessions, they go into Bertram's room to get their stuff back. Emma, Ravi, and Zuri become shocked that Bertram has been hoarding junk. Jessie and the kids agree to help Bertram clean up his room and clear out all of the unwanted junk.

Episode 16
Fri, Apr 13, 201223 mins
Someone switches Mrs. Chesterfields shampoo with glue. She blames the Rosses because they had all ridden together in an elevator recently. Ravi interrogates everyone: Zuri has paper glued all over her hands, but it's only because she did origami. Emma glued her hand to her phone, but it's because she broke it and fixed it. Luke used it to glue Bulls eyes to Bertram's butt. Bertram used it to glue the trophy he broke back together. Finally, they find mrs. Chesterfields shampoo in jessies purse. To prove herself innocent, she looks at the security camera and finds that mrs chesterfields dog switched them. Jessie skips her date to help chesterfield get the glue out but succeeds in getting glued to her and ripping out her hair.

Episode 17
Fri, Apr 27, 201223 mins
Emma likes a bad boy, and Jessie does not approve of her seeing him. Emma rebels and sees him anyway. Jessie worries that Emma will get hurt like she did years ago. Emma throws a party, and her and Jessie talk about boys and have a bonding moment.

Episode 18
Fri, May 4, 201223 mins
Zuri enters the Little Miss Big Apple Pageant.

Episode 19
Fri, May 11, 201223 mins
Nanny Agatha's twin sister Angela arrives from England, and seems to be the opposite of everything Agatha is, until Jessie begins to suspect that the girl is trying to steal the kids and Tony from her. Elsewhere, Emma is horrified to find a massive pimple on her nose.

Episode 20
Fri, Jun 8, 201223 mins
Jessie and Tony have their fourth first date on the Rosses terrace, which Emma and Zuri recreate to look like Jessie's senior prom. However, things go badly when Luke, Ravi, and Bertram are all trapped in a giant teacup advertisement, so Jessie and Tony have to save them.

Episode 21
Fri, Jun 22, 201224 mins
Jessie refuses to let Zuri see a scary movie with Emma, they go behind Jessie's back and they watch the scary movie. However, Zuri ends up getting nightmares from watching the movie and she starts sleeping in Jessie's room, but this becomes complicated for Jessie after getting no sleep. Jessie reveals to Emma and Zuri about her fear of port-a-potties. Both Jessie and Zuri deicide to help each other out on facing their respective fears, it becomes a success for both of them. Meanwhile, Ravi develops a crush on a girl, but he becomes dismayed when his crush likes his brother. Ravi challenges Luke to a duel in the park. Elsewhere, Bertram has been listening to an opera station non-stop, so he can win a trip to Italy, he becomes upset when he wins a trip to New Jersey. In the end, Jessie and the Ross kids try to get the port-a-potty down to the lobby, but they become horrified when Bertram uses the port-a-potty.

Episode 22
Fri, Jul 13, 201223 mins
Jessie, Bertram and the Ross kids head to Bali, Indonesia for a family vacation, but when their private jet and the whole system starts to fail, Jessie tries to take control of the private jet cockpit and makes an emergency landing on a tropical island in the Pacific Ocean. Now, Jessie must figure out how to get Bertram and the Ross kids back home to safety, while recovering from all poisonous insect bites, escaping from the wrath of scary monsters, and then, tracking down Ravi's pet lizard, Mr. Kipling.

Episode 23
Fri, Jul 27, 201224 mins
Jessie directs a play she's written at the kids' school.

Episode 24
Fri, Aug 10, 201223 mins
Jessie decides she wants to try acting and plans on auditioning for a show.

Episode 25
Fri, Aug 24, 201224 mins
Jessie plans Zuri's Gotcha Day: the day her adoptive parents brought her home. As the kids talk about adoption, Ravi learns that when Christina and Morgan got him, they were expecting him to be a baby.

Episode 26
Fri, Sep 7, 201224 mins
Ravi notices odd behavior from Mr. Kipling.
