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.

Hilary lands a new job as an assistant to an actress, Marissa Redman who turns out to be completely disrespectful. Will surprises Hilary with Jazz in the office and Marissa takes a liking to Will, wanting to bring him to a restaurant opening and threatens Hilary with being fired in order to set up the date. Will agrees, but only if Hilary goes on a date with Jazz. Marissa gets mad at Hilary for not giving someone champagne when Jazz acts up and gets mad at Marissa for talking to Hilary like that. At home, Hilary thanks Jazz by kissing him.