She and Jessie have a very close sisterly-like relationship

Jessie gets worried whenever Zuri talks to her imaginary friends too much or doesn’t do her homework at all, but Zuri still listens to her. eventually. Jessie always has her back whenever she gets bullied. For instance, in the World Wide Web of Lies, Jessie defends Zuri when she gets harassed by Agatha and Axel. At other times, Jessie tries to get Zuri to listen to her, but almost every attempt fails, like in Badfellas, Zuri refuses to leave her tree, Branchy, in Central Park, no matter how many times Jessie forced her to do so. Also, Jessie was the only one to find out about Zuri’s amazing chess skills. Overall, they have a wonderful friendship. (See Zessie)

Bertram Winkle

Jessie often comes to Bertram for advice regarding helping the kids out with their problems. Bertram usually gives her answers that involve being lazy, but they give Jessie good ideas. While Bertram shows himself to not want Jessie around, he thinks of as family, and he truly does care about her as a friend and is even willing to walk her down the aisle posing for her father on her wedding day (There Goes the Bride). (See Bessie)

Tony Chiccolini

They meet in the pilot episode when Jessie first becomes the nanny to the Ross kids. In the third episode, Tony asks Jessie out on a date. Jessie doesn’t want to date anyone she works with because she worries about the awkwardness there would be if they were to break up. Tony tries to kiss her but she avoids him. Soon afterward though, she realizes she has feelings for him and they begin dating later in the season. They have their first kiss in the episode Tempest in a Teacup. In Break-Up and Shape-Up, they decide to break up but remain close friends. They also admit they will always love each other. They still get along really well together after initial awkwardness right after breaking up. Tony still has feelings for her. They got back together in The Ghostest With the Mostest. (See Tessie)

Brooks Wentworth

They first met in the first part of the Season 3 finale “Between the Swoon & New York City”. They started dating in that episode and, soon after, got engaged. They broke up in the final part of the finale “There Goes the Bride” because she wasn’t ready to share her life with someone else. In the Season 4 episode, But Africa Is So. Fari!, Jessie is convinced that Brooks isn’t over her. The kids take her to Africa because they think she isn’t over him. There, they learn that Brooks actually has a girlfriend Kami and is completely over Jessie. Kami and Brooks even have an inside joke about Jessie. (See Bressie)

In “Jessie Goes To Hollywood”, she finally gets her big break as an actress, thereby leaving New York and her charges to go to Hollywood. Her career and further relationship with the Ross kids are unknown, as well as the relationship between Tony and Jessie.

Career

Jessie Prescott used to work as a nanny to a rich family. She moved to New York City in the first episode after already telling her father she had a job. She didn’t however and she soon meets the seven-year-old Zuri Ross. Zuri then brings her into her penthouse and asks her to be her and her siblings’ nanny. After much consideration, and approval from Mr. and Mrs. Ross, Jessie Hookup accepts the position. Every now and then Jessie gets into trouble and worries if she might lose her job but the Ross parents know she tries her best and loves the children very much. Jessie’s dream job is to be an actress. She has tried getting multiple jobs in anything from commercials to plays, to TV shows, but usually these end in disaster. In Jessie’s Big Break, she made friends with a famous actress, Shaylee Michaels and got a job as a stuntwoman even though she wasn’t technically registered as one. Jessie finally got her big break, when she gets to be a lead on a new tv series about a superhero and gets to become a nanny to children as a cover in the series finale.