Jessie hits it off with a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield's son.

Unhappy with her son's budding relationship, Mrs. Chesterfield hires Bertram; she's hoping he finds dirt that will cause Brooks to break up with Jessie.

The Halloween Festival takes a scary turn when Brooks proposes to Jessie and she learns that none of the Ross kids approve.

Jessie and the Ross kids plan a tropical Christmas at the family's Hawaiian villa where Jessie reunites with old friend and superstar, Shayelee Michaels.

In the season four premiere, the Ross kids are convinced Jessie is headed to Africa to rekindle her relationship with ex-fiancé, Brooks. In an effort to stop her, the kids make the trip to Africa and quickly find themselves on a wild adventure.