In the spring of 1960, the Academy hired a new headmaster; his name was Randy White, the only man who had denied Owens's personal interview.

As seniors at the Academy, Owen and Johnny are allowed to take the train to Boston on weekends if they chose to do so. Using their fake draft cards, Owen and Johnny attend a local strip club, which Owen finds to be "disgusting" and "degrading". Johnny then begins to realize just how deliberate Owens’s actions really are. They find themselves on Newbury Street where Owen takes an interest in a local clothing store window. The store's name is Jerrold’s, and it is the store where Tabitha got the red dress that she hated. Johnny and Owen enter the store and begin questioning the owner and his son about Tabitha. The storeowner, upon looking at a photograph, which Owen has brought with him, remembers Tabitha as a local singing talent called "The Lady in Red". The owner of the store (Mr. Giordano) tells Owen and Johnny that Tabitha used to sing at a local supper club whose name he can't remember.
             Later that year, Owen and Johnny are talking to Larry Lish, another student at the Academy. Larry Lish tells them that President Kennedy has been having an affair with Marilyn Monroe. Mitzy Lish (Larry's mother) tells Owen that JFK is indeed having an affair with Marilyn Monroe, she them proceeds to insult and embarrass Owen by taunting him. Owen responds by making a rude remark about Mitzy Lish. . She then tells the headmaster and the incident lands Owen on probation. One Saturday morning, as Owen was arriving to his job as a faculty waiter, Owen notices Dr. Dolder's Volkswagen Beetle sitting parked near the Main Academy building. At the same time, a large portion of the basketball team walks by, on their way to the team bus to go play an away game. Owen convinces them to lift up the car and put it on the stage of the Main Academy building. Pastor Merril questions Owen about the car, only to steer suspicion away from him, but the headmaster knows that Owen is responsible. Mr. White, however, is unable to pin the blame on Owen and Owen gets away.