Grace and Tom's relationship is exposed when a fellow professor catches them kissing in her office. Later in the evening, Peter turns to Grace for advice when he finds out Courtney is having sex with her boyfriend. Meanwhile, Jack's relationship with Katie progresses and in an effort to become popular at school, Bobby and Warren decide to have sleep over and come up with a shocking idea to make the evening memorable.

Jack and Katie's relationship progresses, while Courtney's comes to a screeching halt after Jack discovers Nate is cheating on her with another girl. When Bobby is required to do a family history project for class, he goes through his mother's closet for clues about his family and discovers a letter that reveals the real reason his father left. Meanwhile, Grace is shocked to learn that her affair with Tom has cost her more then she had bargained for.