A mother sends her teenage son to live with his wealthy relatives in a California suburb where the up-scale live.
Ashley tells Will that she does not like playing the violin, and he trades her violin with drums.
Will wants to impress the father of the girl he likes so that he can date her, and Geoffrey teaches him how to act like a proper gentleman.
Philip wins an important prize, but Will causes great embarrassment to Philip when he tells funny tales about him.
Will is visited by an old friend named Ice Tray, who tries to get close to Hillary.
While Philip and Vivian travel to Palm Springs, Will and Carlton take Furth's car and get pulled over for stealing it.
Will enrolls in an after-school program and tries to come up with a poem in order to gain the admiration of the girls.
As the family heads to the mall to get costumes for Hilary's Halloween party, Will and Carlton bet on who can win a date at the party.
Will and Carlton both try to impress Melinda by fabricating stories about themselves.
Will decides to set Geoffrey up on a blind date as a gift for his birthday, but Geoffrey eventually thinks the girl is a better fit for Will.
Will becomes increasingly popular in school thanks to his basketball skills, and he begins to ignore Carlton.
Will gets a visit from his mother for the holidays, as she begins preparing for Thanksgiving dinner.
After Hilary rats Will out for staying up late in order to get the family car, he decides to get revenge.
At their slumber party, Ashley and her friends want Will to tell them a spooky story.
Will tries to give Ashley a special Christmas experience, as she never really had one.
Because of a few coincidences, a superstitious client of Philip's befriends Will.
Will attends a class on the history of African Americans at Bel-Air Academy and is surprised by the attendance of Aunt Viv.
Philip's mother stays with the family for the weekend after recovering from a cold, and Philip asks her to rest.
Jazz asks Will to take his sister out on a date after she moves into town.
Will wants to get the car from Philip and Viv to head to a Ziggy Marley concert in Nevada.
Will futilely tries to impress Kayla Samuels, one of Vivian's students, when she comes over for dinner.
As Vivian travels, she leaves Hilary in charge of the house, and Will steals the keys to the car and ends up losing it for a bet.
Will makes a bet with Carlton that he wouldn't last a weekend in the neighborhood where Jazz lives, Compton.
Will and Carlton are at odds with Ashley's date who comes to perform at her birthday.
Hilary gets a new job as an actress's assistant. Will and Jazz surprise Hilary at her office, and the actress admires Will and tries to go out with him.