Jessica--as well as everyone else--is surprised when she gets one of the highest scores on the college compatibility test. Her and Mortimer are chosen to represent the school in the academic bowl, and even though Jessica finds out that her test results were wrong, she decides to participate anyway. When Winston angers two guys--Todd's 'friends'--they demand two hundred dollars from him, which he doesn't have. Elizabeth decides to help him out and give him the money to pay them, but Jessica uses the money without asking to buy a new dress. Cheryl tries to help out Winston by teaching him boxing, just in case those two guys want to fight him.