The episode begins with Jerry, Kramer and Elaine dining at Monk’s Cafe. George enters and says, “My mother caught me.” When asked what, he says, “I was alone,” and he goes on to imply that his mother caught him masturbating in her house while reading Glamour Magazine, resulting in her falling over in shock and ending up in the hospital. George says he’ll never do that again, and when Jerry expresses skepticism at this, they make a $100 bet over who can go the longest without masturbating. Kramer then joins the bet, as does Elaine. However, Elaine is forced to bet $150, because the men claim that it is harder for men not to masturbate, as it is part of a man’s “lifestyle”.
Kramer is first out, due to the presence of a beautiful woman in the apartment across the street who walked around naked with the curtains open. The others are distracted by various temptations. George is distracted in the hospital his mother is staying at by another attractive woman who receives daily sponge baths from an equally attractive female nurse. Elaine attends a fitness club which is also attended by John F. Kennedy, Jr. Jerry is tempted by the naked woman across the street and frustrated because the woman he’s dating won’t have sex with him, since she is a virgin.
The contest affects their sleep, and the remaining contestants suffer insomnia, while only the people who were eliminated can sleep peacefully. Elaine shares a ride with Kennedy, and she tells him that she lives near Jerry in order to extend the ride. She then learns that Kennedy wants to meet, and says he’ll drop by Jerry’s apartment. Eventually, the pressure becomes too much for her and she is the second person to be knocked out of the contest.
While making out on the couch, Marla asks Jerry if they can have sex, claiming that she is ready. However, Jerry then tells Marla about the contest, prompting Marla to leave in disgust. Elaine believes that Kennedy has changed his mind and not bothered to see her. George then tells Elaine that Kennedy did come, but missed her and went with Marla. They then see Kramer with the naked woman across the street. That night, everyone has a good sleep, implying that nobody won, but there are two later references in the series to George having won. First, in “The Puffy Shirt”, George has a brief new career as a hand model, and is warned about a previous model that ruined his career by deforming his hands through too-frequent masturbation. George replies: “You don’t have to worry about me. I won a contest.” Second, in The Finale, George is shown to be the victor, but thinking he’s about to die in a plane crash, he admits to Jerry that he cheated. Marla also is found, showing that she slept with John.