Unwrapped (2001)

S1E30 The Mating Game

Donald is assigned to cover the show "The Mating Game," and enlists Ann as one of the contestants, keeping his identity as a bachelor a secret from her. During the show, Ann ends up choosing a different man for her date. Meanwhile, Donald decides to accompany them to gather material for his story, creating an awkward yet intriguing situation as he watches from the sidelines.