Hemingway has played a lesbian or bisexual woman in several movies and television shows, including, "Personal Best", "The Sex Monster", "In Her Line of Fire", and episodes of the TV series "Roseanne" and "Crossing Jordan". Hemingway, however, is not gay. She has said she formed a "big connection with the gay-and-lesbian community" after "Personal Best" and enjoys taking roles in "cutting-edge" productions.