In the shadow of the Kavanaugh Supreme Court nomination hearings, we discuss how far back we should be held responsible for the sins of our youth. We discuss a firing of a high school Spanish teacher who had posed for Playboy when she was 19 years old. We also discuss other real, past scenarios involving members of the panel. We review the HR implications and some of the relevant laws. We also talk about the contradictory nature of the cultural environment of permissiveness and zero-tolerance for mistakes. We conclude by examining how Catholic parents can help their children maneuver these complicated times, especially in light of the impact of social media.