Philip and Vivian take a weekend vacation and leave the kids home alone, Hilary and Carlton set up a video shoot with Bell Biv De Voe in their house, and then everyone must rush to clean up after Philip and Vivian decide to come home early.
Will gets lucky at a fund raiser and wins some money. When Will doesn't follow the clubs tradition, it starts rumors about the Banks family. Ashley is too young to go to the fund raiser so her and Geoffrey set up their own poker night.
Will has a game coming up with Malibu Prep in which a scout will be in the crowd. He meets a player from the other team. After learning that Marcus has a child Will must choose between being greedy or realizing what the scholarship would mean to Marcus.
Geoffrey falls for the woman next door while thinking she is a butler. When he finds out she is just visiting and is worth 25 million dollars he must decide whether he wants to continue seeing her, or not.
Vivian trusts Wil and Carlton to take her heirloom bracelet to the jewelry shop to have it reset. Before they do that, Carlton tells Wil about a hot insider tip he got on a company's stock, and they can make thousands. They don't have the money to buy the stock, but the boys figure the appraised value of the bracelet will easily cover its cost. So, they take it to the pawn shop and sell it, then buy the stock. That night, they watch a news report where the company has announced bankruptcy. Uh oh - now not only have the two lost money on a bad tip, they don't have any ...