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14 hours ago · Max is a trans man and Tiffany Prigent's boyfriend. Erica Bettis. Helen Shaver. The Education of Max Bickford. Trans woman with a Ph.D. [32] (2001-2002) Bill. Chris O'Donnell. Two and a Half Men. In the episode "An Old Flame With a New Wick" O'Donnell plays a trans man named Bill and the ex-boyfriend of Charlie Harper.