One of Vivian's students, Kayla Samuels comes over for dinner and Will tries to impress her but fails. Eventually, Will wins her over and inadvertently starts taking time away from her studies so Vivian tells him to cut back on their relationship so Kayla can have a good future. Vivian winds up lecturing Kayla and revealing things about her own struggles to be successful.

Will makes a bet that Carlton wouldn't last a weekend in Jazz's neighborhood, Compton, because of the way he is. Carlton takes the bet too far by becoming very thug-like, wearing colorful clothing, shades, and bandanas (like Will), and Will has to find a way to stop him from going to MacArthur Park at night. He then rats on him to the parents, and they go to rescue him before going to the park. At the house, Carlton wins the bet, and the reason he won is because Will cared about him and didn't want him to possibly die at the park that night.