Brooks Wentworth is the former fiance of Jessie Prescott in the season 3 finale. He is also the son of Rhoda Chesterfield. He is portrayed by Peirson Fode.
Jessie's relationship with Brooks was foreshadowed at the end of Creepy Connie 3: The Creepining when Jessie catches the bouquet at Luke and Connie's Brooks fake wedding and says "Better not take down those decorations on the terrace cause Jessie's gonna land herself a man!". Brooks first appears in New York and the Swoon when Jessie first bumps into him in the park. They quickly form a mutual attraction and Brooks arrives at the Rosses penthouse to ask Jessie out. When Mrs. Chesterfield finds out they are dating, and is Brooks' mother, she takes extreme measures to break them up as she does not approve of Jessie. After Brooks stands up to his mother, she strips him off of his money and leaves him broke. In No Money, No Problem, Jessie helps Brooks by getting him a job as the elevator operator of the building. Mrs. Chesterfield still wants to break them up, but after some probbing from Bertram she finally agrees to accept her son's decision and returns his money. Near the end of the episode, Brooks proposes to Jessie. In The Runaway Bride of Frankenstein, Jessie takes some time to think about Brooks' proposal. Brooks tries to impress her by helping out the Ross kids on a Halloween party, with disastrous results. In the end, Jessie has a dream where Brooks (as a Frankenstein's monster) acted very disruptive on a rampage. From this point, she concludes there is no such thing as "the perfect guy" and accepts Brooks' proposal. They become engaged. However, as they preparing for their wedding, Brooks gets offered a position at an animal sanctuary in Africa. He asks Jessie to come with him but, unwilling to leave the kids and her dream of acting, Jessie refuses. They break up shortly after.
In But Africa Is So...Fari, it is revealed that Brooks has a new girlfriend named Kami,who is also his assistant in the animal sanctuary. Jessie was clearly upset about this, but she told Kami it is so okay for her date Brooks and taunts her for when she meets Brooks' mother.
Tony is Jessie's ex-boyfriend in the first two seasons. When Jessie started dating Brooks, Tony was jealous as he still has feelings for her. Although, he did help Brooks while he was broke and hired him to work as an elevator operator in the building. He was going to tell Jessie how he feels at the end of No Money, No Problem, but ended up watching in despair as Brooks proposes and left humiliated in the elevator. In There Goes The Bride, Tony was the minister at Jessie and Brooks' wedding although he was initially reluctant about attending due to the "exes not allowed at weddings" policy. When Jessie left Brooks in the same episode, Brooks believed it was because of Tony hinting that the jealousy is possibly mutual.