An idealistic teen from rural Texas embarks on the adventure of a lifetime when she decides to leave behind starry nights for big city lights. Thrilled to be on her own and determined not to be intimidated by New York City, she accepts a job as nanny for a high-profile couple with four kids. Helping to keep her moral compass in check are Bertram, the family's butler, and Tony, the building's 20-year-old doorman.
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.
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.
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.
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.
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 decides to pursue acting, so she auditions for a TV show.