We compete in the craziest round of Easy Trivia as Bobby sets a new stipulation. In the Anonymous Inbox, a dad wants to know what to do after he was just trying to be a good dad but his son calls him cringe. Amy and Eddie give their advice and we wonder if they are just as cringey to their kids. Bobby talked to Randy Jackson and he had a challenge to propose to him.  Bobby shares what he assumes each person on the show would get arrested for. We also share what we think Bobby would get arrested for.  Tim McGraw stops by the studio to talk about our iHeartRadio Music Festival, his newly bald head, the ending of Don't Take the Girl and recording Over and Over with Nelly.