Two And A Half Men: Season 1, Episode 18

1 - 18: An Old Flame with a New Wick

Charlie goes to meet his ex-girlfriend, Jill, but he is stunned when he learns that Jill is now a transman (Chris O'Donnell) called Bill. Berta takes great enjoyment out of the situation, especially when it turns out that Evelyn is also dating Bill. Title quotation from: Berta, about Charlie's ex-girlfriend who has had a sex-change.