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Jessie Prescott (Debby Ryan) arrives in New York, where she is dumped out of her cab at the Ross's condo building (The Fairfield) and meets a little girl named Zuri (Skai Jackson). Witnessing her Nanny Kate run 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 (Kevin Chamberlin), a sarcastic, lazy butler and adoptive parents, Morgan and Christina Ross. They hire her to be the a nanny to Zuri, Ravi (Karan Brar), Luke (Cameron Boyce) who gets a crush on Jessie, and Emma (Peyton List). 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 can't attend her science fair. Jessie goes to the movie set 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. Emma wins the science fair, and Jessie is rehired. Each child attempts to give Jessie another chance.

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, he gets a lot of credit even though he did nothing towards the report. Also, Zuri gets bullied by one of her imaginary enemies, Genevieve.

After Jessie accepts an invitation for lunch with Tony (Chris Galya), the building's doorman, Emma offers Jessie unsolicited love advice she reads 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.

After Jessie embarrasses Luke in front of a bully,(with sunscreen, a pink bicycle helmet, and cradling him in her arms), he doesn't 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 (not including Ravi, who Luke chose from "the bottom of the barrel"). 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.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 spend the day with Zuri after he had been the unwanted guest at the tea party for the last little while of the show.

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 their neighbor Mrs. Arthur, but she arrives at the penthouse in character as "Nana Banana", a former clown with a colorful personality. Zuri begins to favor Nana over Jessie. Jealous, Jessie throws Nana 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 steal it from the park while trying to avoid Ranger Bill (Ronnie Schell), the nearly-blind park security guard. In the end, they get caught, but Nana Banana smooth talks the ruff and burly park security guard.

Jessie believes that Connie (Sierra McCormick), a math tutor she finds for Luke, will be the perfect scholarly influence, not realizing that "Creepy" 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. Meanwhile, Ravi is convinced that he can predict the future with his Mystical Eye-ball Application on his tablet. Zuri doesn't believe him at first, but after asking a question that gave her an unpredictable answer (Mr. Kipling destroying her pet pony stuffed animal), Zuri finally agrees with Ravi's Mystical iBall app. And so, once these younger Ross siblings hear of terrible predictions about Bertram's fate from the Mystical eye-ball app, they try and convince Bertram to stay alert.

Special guest star: Sierra McCormick as Connie

The Ross children are beyond excited for their parents' arrival; they make sure the house is decorated to perfection. Meanwhile, Ravi has never heard of Santa, so Zuri explains who he is, except that she makes him sound like he is a judgmental spy who feasts on children. When Christina and Morgan cannot make it because they got caught in a snowstorm, it is up to Jessie and Bertram to bring the Christmas spirit to the children.

Celebrity actor Jordan Taylor (Lachlan Buchanan) comes to stay at the Ross household. Jessie and Emma fight for his affection, while Luke and Zuri make prank phone calls on his phone. Bertram pretends to work while Morgan Ross is in town. Even though Morgan tells everyone not to tell people that Jordan is staying at the Ross penthouse, Emma tries to ruin Jessie's date with Jordan, disobeying her father's orders.

After Zuri's doll is ruined, she and Jessie attempt to raise two hundred dollars for a new one, despite attempts on being stopped by a cop and Mrs. Chesterfield. Meanwhile, Ravi starts as the new student in Luke and Emma's school, although Luke expects him to act normal on his first day. Despite trying to fit in, Ravi's first unexpected attempt to embarrass Luke led him to lie to his friends about Ravi (Luke's "dad's friend's cousin's dog's neighbor"), because of his geeky cricket uniform. Luckily, Ravi helps stop a school bully when he has him eat one of his dragon fire peppers.

Jessie competes with another nanny named Agatha (Jennifer Veal), who forbids her from taking the Ross children to Central Park. Agatha writes on her website, Toddler Tattler, about Jessie and what a bad nanny she is by posting pictures of Jessie brushing dirt off of Zuri's rear end. Agatha twists the truth and writes that Jessie always spanks Zuri and that was proof. However, it was libel since the picture was taken by Agatha herself when Zuri fell in the dirt. When Christina finds out about the website, she believes Jessie and does not fire her; instead she helps her get rid of Agatha. Meanwhile, at the penthouse, Bertram is sick and tired of Luke and Ravi constantly "nurpling" each other, so he teaches them a lesson by teaching them how to wrestle.

Jessie leaves Emma in charge of Luke and Ravi, as Emma helps her brothers search for what they think are strange noises coming from the dumbwaiter shaft. Ravi attempts to go forth and search for this mysterious creature, shocking him once he finds it. When Ravi doesn't return back to the kitchen for quite a while, Luke dresses up like Indiana Jones to go and search for him, but they are terrified when they find a load of animal bones and it gets dark. Emma also tries to help, but gets herself lost in the walls, making Luke finally explode in fury. Apparently, it turns out that the strange noise is Manny the Mongoose, Mr. Kipling's chew toy, and that the shafts are where he gets rid of the indigestible bones of his bread. Mr. Kipling then leads Emma, Luke and Ravi out of the shafts into Ravi's room. Meanwhile, Jessie auditions for a role on a television show, yet Zuri is the one who impresses the director instead. Jealous and angry that she didn't get the part, Jessie tries to squirm herself into the spotlight, thus creating a Ross diva instead of fulfilling her acting dream. The producer gets mad and fires Zuri and Jessie.

Rumors whisper over to a man named Grimm Holloran, a doorman with a strange personality. Grimm warns the Ross children not to trick-or-treat on the 13th floor, for there are dangers beyond understanding. Too brave and cocky to believe in such words, Luke decides to trick-or-treat on the 13th floor with Zuri, despite Emma and Ravi's deep fear of Grimm's warning. Meanwhile, Jessie plans to submit her story to a famous newspaper journalist. Unfortunately, her abnormal tactics cause the Ross children to believe that she is a bloodthirsty maniac waiting to kill off anyone in her path. Tony tries to calm her down throughout the episode, but to no avail.

Mrs. Kipling's baby lizards have brought a lot of chaos in the Ross household. Ravi has barely gotten any sleep and he is constantly tired. He contracts Zuri as his part-time nanny in order to help him with the babies. Unfortunately, this causes a rift of trust between these two siblings, Zuri doesn't treat them well. Meanwhile, Jessie and Tony go out on a date which Officer Petey crashes, much to Tony's dismay. Later, Jessie joins a comedy improv class alongside Petey. Tony is jealous because she is spending a lot of time with him, so he asks Emma to help him discover if Jessie is cheating on him by spying.

It is the beginning of the school year; Jessie and Bertram could not be happier. On Emma's first day of high school, she meets a rude, aggressive girl named Rosie (Kelly Gould). To Emma's dismay, they are assigned to do an art project together and Rosie ends up embarrassing her. Meanwhile, Luke searches through his backpack and Kenny the Koala accidentally falls out. Random bullies witness the incident and laugh at him. Ravi takes the blame in order to leave Luke off the hook; unfortunately, they start teasing him instead. Elsewhere, Zuri is upset because she has just started third grade and her homework is more difficult, so she refuses to do it. Feeling guilty and upset, Rosie attempts to apologize to Emma for embarrassing her, Luke reveals to everyone at Walden Academy Middle School that he owns Kenny, not Ravi, as the brothers kindly embrace, and Zuri reveals why she didn't complete her homework, forcing Jessie to cheer her up.

When Ravi realizes he cannot possibly take care of his twelve baby lizards, Jessie persuades him to give them out for adoption. After Ravi interviews many people, he does not approve because he wants to find the lizards good parents. Finally, a woman named Cassandra is interviewed and mentions how her boss is going to take them upstate to a loving home. Jessie and Ravi are horrified when they discover that Cassandra's boss is Ms. Chesterfield. After a few misunderstandings, Jessie and the children are convinced that Ms. Chesterfield is turning the lizards into accessories, so they embark on a journey to rescue the lizards. As turns out, Mrs. Chesterfield was actually going to set Mrs. Kipling's babies to live in her lizard sanctuary.

Christina returns to promote her new retro-80s clothing line, Fersher Couture, at the same time Emma's new anonymous fashion blog, Kitty Couture, is trending. When Emma looks at her over-the-top designs, she does not want to give her mother an honest review in order to spare Christina's feelings. Meanwhile, Luke and Ravi compete to impress international supermodel, Diamond Bloodworth. Elsewhere, since Jessie is working as Christina's assistant, Bertram takes over the duty of being the nanny and watches over Zuri. When Zuri finds out Bertram can't ride a bike, she becomes determined to teach him how to ride a bike.

Emma is beyond excited when she finds out that Austin Moon (Ross Lynch) is performing at Times Square. On New Year's Eve, Jessie takes her to see Austin and to their luck, they bump into him, and meet the rest of the gang: Ally (Laura Marano), Trish (Raini Rodriguez), and Dez (Calum Worthy). Plus, Jessie comes up with a brilliant plan on how to get Austin to perform on time. Later on, the gang shows up at their apartment, and Emma tells Jessie that if she helps them, he could record one of her songs and turn it into a big hit. When Ally reads Jessie's lyrics, she thinks they are not good, so Jessie accidentally steals Zuri's poem and takes credit for it. In the end, when Austin and Jessie are about to perform in Miami, she gives Zuri credit, and everybody is satisfied with Dez' impressive music video.

Songs featured: "Christmas Soul", "Can You Feel It", "Face 2 Face"

Jessie is worried that Tony will propose after he invites her out for a special evening to meet his parents, so she drags Zuri and her new friend to the dinner to keep him from doing anything romantic. Meanwhile, a boy named Stuart develops a huge crush on Zuri and she gets annoyed by him. Elsewhere, Emma & Bertram compete with Luke & Ravi to see who really owns the Ross Screening Room. Sadly, this causes a rift of trust between the pairs as they all seek revenge on each other. Luke & Ravi wind up trapped outside on the terrace, barely surviving and almost freezing to death. Emma and Bertram end up trapped in a rope net, Zuri tries to help them down with some children's scissors to cut the rope lines and says that it takes hours to cut paper with it.

Jessie introduces the children to Miami Heat player Chris Bosh who is going to be playing the New York Knicks. In order for the Knicks to win, Luke washes out the luck of Chris' socks so he loses. Later on, Chris starts to lose his skills in basketball to Luke's dismay. Meanwhile, a famous fashion designer sends Emma a dress to review on her fashion blog; however, things go awry when Jessie accidentally damages the dress.

Zuri is having problems with her teacher, Ms. Folkemburg (Cheri Oteri), so Jessie decides to volunteer as the classroom aide. Jessie tries to become the teacher's pet, but accidentally ends up becoming her best friend. Now, Jessie has to go along with it in order for Zuri to do better in school. Meanwhile, Ravi has issues with Mrs. Kipling, causing him to stay in Luke's room for a couple of days. Worried about Ravi's self-being and sanity, Luke enlists Emma & Bertram to help him get rid of Ravi by insulting Mrs. Kipling.

Jessie gets her big break as a stunt double to famous Australian actress, Shaylee Michaels (Maia Mitchell), and the two become fast friends. Chaos ensues when the movie's director, Shaylee's boyfriend, McD (John DeLuca), starts flirting with Jessie. McD turns Jessie against Shaylee by saying that she was lying to her. Luckily for Jessie, Luke records McD flirting with Jessie and Jessie and Shaylee become friends again. Meanwhile, Emma and Ravi help sneak Zuri's pet zebra, ZB, into the penthouse, but after they get caught, they also end up losing Mrs. Kipling. Now, they must set out and save Mrs. Kipling from the maniacal zoo caretaker Ms. Lumpkey (Suzanne Krull).

Guest stars: Maia Mitchell as Shaylee Michaels, John DeLuca as McD

Emma & Luke teach Bertram how to salsa dance in order to impress the building's chef, Salma Espinoza, but Bertram's confidence gets hold of him, as he keeps saying sadly, "I can't do it." But Luke and Emma are determined to teach Bertram. Meanwhile, Zuri trades Jessie's childhood doll for a bunny that gives chocolate. Angry and upset, Jessie ignores Zuri until she apologizes, with Ravi gloating. The trio comes up with a plan to retrieve Jessie's doll. At Central Park, Bertram dances with Salma happily after gaining his confidence back, but it leaves him again one he notices the judges staring at him. Emma pleads Bertram to look inside of himself and say that he can do it. Luke shows off his dancing skills with Salma as his current partner. In the end, Emma & Luke win the trophy as the best salsa dancers in Central Park (so far). Also, Jessie retrieves her precious Mary-doll and hugs Zuri with Ravi smiling.

A package arrives for Ravi with a bell in it. He claims the bell has magic powers. When Zuri and Jessie are both holding the bell and arguing with each other, it causes them to switch bodies. Then Emma and Luke switch bodies under similar circumstances, and next Ravi and Bertram switch bodies. The body transfers result in many problems. Emma needs to be back in her own body to shoot her Kitty Couture web show, and Luke doesn`t like Emma acting girly in his body. When Ravi and Bertram switch bodies Ravi gets freaked out because Bertram is obsessed with having hair and keeps stroking it. Zuri acts very childish while in Jessie`s body, and Jessie has trouble getting Zuri to listen to her, as Jessie has her first big acting role and needs Zuri to cooperate. During Jessie`s performance, Ravi realizes everyone was arguing when they switched bodies, and to switch back must say positive things about one another while holding the bell. He and Bertram switch back, and Jessie runs the bell up to Zuri onstage. After Luke and Emma switch back, Ravi claims he destroyed the bell, but at the end of the episode it appears Mrs. Kipling and Jessie have now switched bodies. It is revealed that the entire episode was just Mrs. Kipling's dream, and when she wakes up just as soon as the package really arrives.

Jessie and Tony's first anniversary is coming up and Jessie wants to write him a song in which she expresses how much he means to her. But when she thinks he has forgotten it, she writes an angry song that is known put on Emma's video blog and becomes hit. The next day Jessie gets invited to do a concert at the park, but finds out that she got the date wrong and Tony gets tickets to the concert Jessie is playing at, so she has Emma stall him. Unfortunately he ends up at the concert, but Jessie is able to tell him she loves him and plays the song she originally intended to sing him. Ravi has consistently poor grades in physical education. Therefore Luke, who is very good at sports, can let him win in a competition to build his confidence. But Ravi has gained a little too much self-confidence. It turns out that Jessie was the one who mixed up the anniversary.

Emma is upset when her friends start to hang around with royally-acclaimed new girl Bryn. Luke chooses to do his multicultural project on India and tricks Ravi into doing his whole project for him. Ravi gets his revenge by re-writing the project and making Luke look like a fool in front of the whole school, but feels bad and helps him recover from his stumble. Since all her friends are busy, Jessie takes Emma to the movies and bumps into her friends with Bryn. While trying to be the bigger person, Emma is teased by Bryn. Jessie finally puts a stop to it after insulting her. A big food fight ensues where the entire movie theater learns that Bryn is not royalty. During the fight, Rosie, one of Emma's friends, "takes" a bunch of nachos by Bryn, which was aimed for Emma. In the end, Emma invites the rest of her friends (including Rosie) over to watch a movie and Zuri tries to tag along.

Jessie wants to prove that she is a great girl scout leader by helping Zuri earn her badges. Also, Emma was in the girls scout too, but the leader of the girls scout found out Emma's badges are fake and she really bought the badges online. Meanwhile, Luke convinces Ravi, that lying is a super power when Ravi lied to Bertram about who is responsible for putting a cricket in his lobster bisque, and continues to lie to him, which put Bertram into more trouble. Jessie makes Emma help Zuri with her badges. Ravi tells (lies) Bertram that his arch-nemesis, Nigel Pettigrew, put the cricket in his lobster bisque, Bertram and Nigel has a "fight" and Nigel wins. Jessie, Emma, and Zuri, get ready to sleep. Coach Penny gets attacked by an ostrich, and gets saved by Zuri, which then allowed her to get a badge. The ostrich attacks Bertram when he finds the orange that Zuri threw.

Emma falls for a cute boy named Brett Summers. But he loves sports and Emma doesn't know anything about sports. So Luke helps her and sits behind the chair and texts Emma what to say. Then Brett finds out and then he forgives her. Then they play a game and then he leaves and tells her that he is studying. But he really went to the screening room with Luke. Then Emma gets mad and breaks up with him. Then Brett watches the movie and gets mad because Luke like hankies and Brett doesn't. Meanwhile, Jessie loses Zuri's pet bunny, of which Bertram is extremely scared. In the end, Zuri's class bunny has babies.

After Emma neglects to pick up Zuri from school and talks back to Jessie about it, Jessie grounds her, telling her she can't go to the school dance. After Ravi tells her that Luke's new crush's ex-boyfriend is going to embarrass him, she sneaks out to warn Luke about it. At the dance, Adam Sandler gives Luke some relationship advice. Meanwhile, Zuri and Ravi set traps to catch a burglar. In the end, Jessie comforts Luke and ends up dancing with him at the school dance.

Guest star: Adam Sandler as himself

Kenny the Koala has always been there for Luke during countless days and nights, until one day, when his "obsession" crosses the line, Luke must make the biggest decision of his life. He can either give up Kenny, or embrace him until the end of his days. Meanwhile, Stuart is devastated that Zuri continuously tries avoiding him, and so he devises a plan to make her jealous by flirting with Emma instead, despite Emma's annoyance. Convinced enough, Zuri does become jealous, and pleads him to get over Emma. Back on the terrace, Kenny accidentally slips out of Jessie's hands as he gets torn up by a car and a horse, causing Luke to go into a deep shock while accusing Jessie for this mess. Near the end, Luke, saddened by Kenny's sudden fall, reveals why Kenny is so important to him, and that he was his only family until Morgan & Christina brought him to the city of New York. Zuri apologizes for taunting Luke all this time, and they have a brief embrace. Stuart successfully fixes Kenny, as Luke thanks him and Ravi for saving his best friend from a near-death experience.

Once Luke, Ravi, Zuri, and Stuart are stranded in the Ross Panic Room with only access to the eight monitor screens of the penthouse's rooms, Luke & Stuart are forced to confess their secrets. Meanwhile, Emma & Bertram support Jessie while she prepares for a TV audition. Unfortunately, this causes Jessie to get trapped in the Panic Room along with the rest of the children, whom she realized were gone for hours.

Bertram's mother visits to celebrate his birthday, but sadly for them, they don't get along very well, as Wanda continuously steals the spotlight, even if she had to go through extreme measures (by shunning Emma & Zuri out of their performance). Furious with his mother, Bertram gives her "the talk" in front of Jessie & the Ross children, while learning how to stand up for himself and his family, thus gaining more confidence to reveal his soft side (love) for the children. Wanda apologizes for her bad behavior as they both happily embrace, making Bertram hungry in the end. Meanwhile the Science World puts the Ross brothers to the test as they're assigned a project which requires an egg. Ravi decides that they should drop the egg and capture its results. Fortunately, Luke perceives this as an opportunity to prove that he is really smart by showing off his outside-the-box thinking. Unfortunately for him, Jessie & Ravi don't accept out-of-the-box ideas, and Ravi claims their science project as his own achievement, which confuses Luke.

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 is hypnotized into thinking that he is a stray tomcat.

Jessie goes with the children to the military base where her father lives and discovers that her father (James Patrick Stuart) is about to be married to the mother of Jessie's high school rival. Meanwhile, Emma falls in love with Darla's (Molly Burnett) brother, Caleb (Dylan Boyack), and Darla and Jessie will do anything to keep them apart.

Jessie and the children are throwing a Halloween party which turned out to be haunted by actual ghosts. Luke and Emma become possessed. Jessie, Ravi, and Zuri will have a plan to save Luke and Emma.

Jessie confronts the children on why they didn't turn in their money from selling muffins for school. The children end up throwing a party, unbeknownst to Jessie, in order to raise the money. But when the children lie about a celebrity guest at the party, Luke ends up going in disguise. Meanwhile Jessie gets an audition for a hand commercial, thanks to her new agent, Max (Matthew Timmons). But when she accidentally puts her hand in purple paint, her attempt to hide it from the commercial producers cause her to get fired. In the end, Jessie tells Max she still wants to work with him.

Jessie gets a role as an understudy to a famous Broadway actress, Susan Channing, but Luke and Ravi sabotage Susan so Jessie can play the part. Meanwhile, Bertram wants to win his own cooking show, so Emma and Zuri try to help out, and end up becoming internet stars after their mishaps in the kitchen get Susan Channing in a mess on camera.

Jessie and Tony set up dates for each other to prove they are moving on. Tony believes Jessie is actually planning to set him up with herself, but when he learns she set him up with her friend, he asks the janitor Earl to take Jessie out on a date, unaware that Earl likes to eat food people throw out. Meanwhile Ravi gets an internship at the zoo, but Luke messes around with the animals when Ravi is put in charge so Emma can take his mentor for a makeover.

When Luke asks Christina about his birthparents, he finds out that his birthmother is a wrestler. Emma successfully helps Luke find this mysterious wrestler, making him slightly emotional afterwards once Luke finds out that his biggest hope was a complete lie. He silently walks away, emotionless and heart-broken after Jessie confronts him with this terrible truth. However, Luke is still concerned about why Christina won't tell him about his past. Christina then explains that she hid this from him because she was afraid of losing his trust and compassion for having such a great mother. A confused yet slightly shocked Luke replies, saying that Christina is already doing an awesome job mothering him, as they share a wonderful embrace. Meanwhile, Ravi plans to run for club president of Walden Academy Middle School's Reptile Club, and he is forced to choose Zuri as his campaign manager (as a permanent replacement for Bertram). However, the sibling duo is surprised that Ravi has an opponent running for the same position. Ravi decides that he'll only be co-president along with his new friend. In the end, Luke narrates his thoroughly yet well-written report about the true meaning of a family.

After Emma, Luke, Ravi and Zuri jump rope an 'award winning' television producer, Corrine offers them a TV show. Jessie gets over-excited and says yes before the children could say their opinions. They all go back to the pent-house and discuss the show. The next day they start filming, and they say that they all love each other but they all say something rude about something or somebody else. Corrine edits their slots making it look they hate each other. They go back to the pent-house and then in the elevator they hatch a plan and decide to be nice but also steal all their footage and upload it to the internet of Corrine being rude to them. That works and Ravi's lizard make them leave by giving them a fright.

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 Teddy meets up with Jessie on the subway. When a blizzard traps P.J and Teddy in New York City, while The Ross children find out that someone took away their Christmas presents and they ask Teddy and P.J. to help them out. Meanwhile in Denver, Bob (Eric Allan Kramer) and Amy (Leigh-Allyn Baker) struggle to know what Charlie (Mia Talerico) wishes for Christmas since they have no knowledge.

When Jessie enrolls Luke in a dance class, the teacher says he is great. To Jessie's dismay, he tells Luke not to do his homework because it gets in the way of Dance Class. Luke quits later because the teacher let Jessie and Bertram only to not get in the way of his dancing but removed them because they are awful, but Luke still went on and won. Meanwhile, Zuri develops a crush on a boy and Emma and Ravi assume it is Tony.

When down-to-earth farm girl Maybelle moves into the Fairfield after winning the lottery, Jessie wants Emma to invite her to her party. However, Emma wants it to be sophisticated, since she has invited her crush, Rick Larkin, to the party. Emma tries to help Maybelle become a New Yorker, but it doesn't seem to work. At the party, Maybelle has become sophisticated, which attracts Emma's new boyfriend Rick, who asks her out. Furious that Rick wants to cheat on Emma, Maybelle hogties him. Rick lies and Emma embarrasses her. Eventually, Zuri tells Emma the truth, and she dumps Rick and starts fresh with Maybelle. Meanwhile, Ravi gets shot down by Mr. Collinsworth, the school music teacher, to join the band, so Jessie, Ravi, and Luke (disguised as Chip Falcon) start their own band with other school band rejects. Jessie thinks they're not good enough, and decides to keep them from playing in the Battle of the Bands by hiding their instruments. When Ravi tells her they just wanted to have fun, she "finds" them, and they play. As predicted, they are horrible, but Ravi's sitar solo, impresses Mr. Collinsworth, who invites him to join the band, but Ravi rejects him. In the end, Mr. Collinsworth joins their band, by playing his cheeks, which is just humming.

Jessie hooks Zuri up with a new girl named Wendy McMillan after seeing a director to get her acting career started. With Jessie she is 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 is 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. However, when she finds out that her brothers have also set up a booth that sells more nutritious items, Emma's instincts suspect that Luke and Ravi want competition, making her upset and frustrated about her work ethic.

Creepy Connie returns shortly after Luke meets a girls named Mackenzie (G. Hannelius). She claims that she is over Luke, and warns him that Mackenzie, who she calls "Mad Mack", has a psycho crush on him. When Luke realises that Mack is obsessed with him, he asks Connie to protect him, but she traps him in the penthouse and tries to force him to marry her. When Mack appears she and Connie reveals that it was all a set-up and she is an actress Connie hired. Meanwhile, Emma leaves her food truck workplace unattended to watch a movie with Zuri and Bertram, but while she is absent the truck is robbed and she is fired. Emma's boss, who is Connie's uncle, visits the apartment to rehire Emma and stops the wedding.

Jessie meets a new friend named Abbey in acting class, but Jessie finds surprising things about Abbey. Abbey copied Jessie's idea leaving everyone thinking that was Abbey's brilliant idea. Abbey then bribes Ravi to fire Jessie in the play, but Ravi double-crosses her and helps Jessie instead. Meanwhile, Luke invites a new member to his crew, whom to his annoyance, Zuri suddenly has a crush on him, which makes Stuart a bit jealous and upset. Emma advises Stuart to be more funny, but he takes her advice a bit too literally, boring Zuri in the process. In the end, Stuart stands up for Zuri, and she thanks him for that. Luke leaves, for this is too intense for him.

Zuri makes a new friend named Taylor, with whom Jessie connects after learning she is a military child like her. Jessie meets her grandmother, who tells her Taylor's birthday is coming up. Jessie and Zuri plan the party, but Taylor gets upset and runs off. Her grandmother explains that Taylor misses her mom, serving in the military, so Zuri calls Michelle Obama and gets her to fly Taylor's mother home for her tenth birthday. The entire Ross family, Taylor's family, and Michelle Obama party in the penthouse. Meanwhile, Emma is in charge of the school pep rally, and Ravi wants to be the school mascot. However, Luke auditions after learning the mascot hangs out with the cheerleaders. Luke shows off his dance moves, but Ravi makes a surprise comeback with rapping skills. However, Luke attacks him, and Ravi ends up losing, but is made the first ever male cheerleader, much to Luke's disappointment.

Guest stars: Lauren Pritchard as Coach Penny, Kyla Drew Simmons as Taylor Harris, Yvette Saunders as Sergeant Harris, and Vernee Watson-Johnson as Mrs. Harris.

Jessie is in need of some extra money to buy her dad a birthday present, so she gets a job at The Empire Skate Building before realizing that Emma is her boss. Emma goes very hard on Jessie, and they argue in front of an important critic that is reviewing the restaurant. Meanwhile, Luke and Zuri raise money to have Jessie "babysit" for children.

Jessie and Zuri discover Stuart is cooler than his old self, because he has a new laid-back "manny" (man and nanny) named Hudson. When Jessie forbids Zuri from hanging out with Stuart after she and Stuart's "manny" get into an argument, Zuri and Stuart run away. Meanwhile, Ravi competes for the talent show, but Bertram wants him to sing and Luke wants him to dance, but he can't do it. So, Ravi does cup stacking at the show and he wins the first-prize trophy.

Jessie becomes frustrated that she cannot land any acting gigs, so she takes matters into her own hands by participating in a 24-hour film festival. She recruits the children to help her direct, shoot and edit her film with Tony, but things get complicated when all the children have their own ideas about what the film should be about.

Ravi's birthday present from Christina and Morgan is a trip into Outer Space. Things go awry when Ravi is left behind and Jessie, Emma, Zuri, and Luke are on the locked shuttle, and Ivan, Bertram, Mrs. Kipling, and Ravi must come to the rescue. At the end, Ravi realizes the whole ordeal was a dream.

Sparks fly when Jessie meets Brooks, and she starts worrying after finding out that he is Mrs. Chesterfield's son. She insists that Jessie isn't right for him, but he stands up to her and stays with Jessie. Meanwhile, Luke loses his special baseball to Ravi. He later trades it for more Yankee items. Bertram is forced to babysit Zeus, only to become appreciative of the dog.

Mrs. Chesterfield tries to break up Jessie and Brooks. Luke, Emma and Zuri learn about Ravi's late History Report and throw him an appreciation day (styled R.A.D.). Emma and Zuri convince Tony to open back up to Jessie, while he also gives Brooks a job at the Fairfield. When Tony tries to talk to Jessie in the elevator, he is interrupted by Brooks proposing to Jessie.

Jessie and Brooks are getting married, but when he accepts a job in Africa, he begs a reluctant Jessie to go with him. Jessie decides to go, but the kids each try to make either Jessie or Brooks regret going with the other. Bertram scolds the kids for being so selfish and they go and tell Jessie that they want her to be happy. In the end, Jessie realizes that she isn't ready to leave the kids, and they both realize their dreams will separate them. Jessie and Brooks call off the wedding and break up.

Jessie scores a role on a show, which shoots in Hawaii around Christmas, so Jessie takes the children. When they arrive, Bertram is renting Christina and Morgan's villa out to Jessie's famous friend, Shaylee, to earn some money.