Oprah Winfrey was the guest on "Watch What Happens Live with Andy Cohen" back in 2013, but she hasn't been back since. During her time on the show, Andy Cohen asked her a question regarding her sexuality. Normally, such questions take place during Plead the Fifth, a game where he asks his guests three potentially private or embarrassing questions and they have to answer all of them. They can only "plead the fifth" and refuse to answer one. "I decided, 'Why don't I throw this out?" he said during "Ask Andy," according to People. "'Maybe I'll throw a bomb out.' And I asked Oprah, 'Have you ever swum in the lady pond?' And she was like, 'No.'" He not only regrets asking it, but also how he asked it. "I asked it so poorly," he said during the panel.

In a 2018 interview on "Today," he was asked if any of his questions were ever too racy. Cohen responded with the Oprah incident without hesitation.