Becker and Jake notice that Reggie is upset about something, but she refuses to tell them why. Becker presses Reggie for details, but she responds with a series of lies before finally revealing the truth.

Becker fears that Reggie may get the wrong idea if he asks her to be his date at a medical fundraiser. Fearing that Reggie will misread his invitation, Becker struggles to find someone else to take to the event. Despite his resistance, his friends insist that he should just ask Reggie. The ongoing pressure causes Becker to recall the first time he was rejected by the opposite sex, as Prequel Monday concludes with a flashback sequence of a 10-year-old Becker asking a little girl to a school dance.

John's waiting room turns into a maze of boxes when Linda orders too many supplies; Reggie becomes attracted to a much younger student and Margaret learns that a former patient died and has included her in her will.