Will is still reeling by being defriended by his now unrequited love, Charlotte Allen. To spend time with Charlotte, Will believes the only way is to "purchase" her at the upcoming senior class slave auction, where the popular senior class members auction themselves off as slaves to younger classmen as a fund-raiser. The one problem is getting enough money to ensure that he can't be outbid. The only one of his friends that has any substantial money whatsoever is Simon, who has $100 given to him by his father which Mr. Cooper expects to get back in his regular $10 per hole golf match against his son. What Mr. Cooper doesn't realize is that Simon has always purposefully lost to him as he is a sore loser, and Simon would rather keep the peace with his father. Regardless, Simon gives Will the money, which means that Simon needs to break the golf peace with his father this year, or else. Jay pleads to go to the golf club with them so that he can use its jacuzzi for a very specific carnal ...