While they don’t have a romantic relationship, they are both friendly to each other

Jessie has fair skin, long light auburn hair with bangs, and hazel eyes. She has a square, plump face and full lips. She has a curvy body. She usually curls her medium-length hair but also can be seen with straight hair in some episodes. She also has a firm, strong, and powerful build. Her outfits are always colorful, and she wears both dresses and blouses, jeans, tights, etc. Jessie’s most worn type of footwear appears to be boots and sandals, and she is very rarely seen wearing sneakers. She’s known to be very pretty. In most episodes, she’s always wearing high heels.

Emma Ross

Emma and Jessie are good friends who tell each other everything. Emma sometimes calls Jessie ugly and says she has a bad taste in fashion but loves her and she becomes mean to her back. (See Jemma)

Luke Ross

While Jessie takes no romantic interest in Luke whatsoever, throughout the first season Luke is constantly trying to ask her out and flirt with her. During the second season, Luke seems to understand that she isn’t interested, but every now and then tries to flirt with her. However, in Diary Of A Mad Newswoman, it can be noticed she’s more interested in his crush on her than she is in other episodes. (See Lessie)

Ravi Ross

Since Ravi is usually picked on by the other kids (Luke is usually the ringleader), Jessie sticks up for him and solves the problem it is shown that Jessie cares for Ravi very much and loves him very much and are good friends. (See Javi)

Zuri Ross

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 tips fastflirting 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)