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Just as Pepper's dating life hits a dry spell, in walks Grady Harper, Chicago's incredibly famous, and available, quarterback. Pepper and Grady are enjoying a romantic dinner when Charlie, Grady's biggest fan, unexpectedly crashes the meal, but Charlie soon notices he is receiving all of Grady's attention. Pepper confronts Grady about his sexual orientation and, along with Charlie, encourages the famous football star to make a big public announcement. Meanwhile, Pepper attends Chick's high school reunion, where music superstar Liz Phair performs.
