Andy Cohen Revealed The One Question He “Regrets” Asking Oprah Winfrey In 2013
Rachel Ellis
Updated on April 04, 2026
As he celebrates 15 years of Watch What Happens Live, Andy Cohen has revealed a “few regrets” throughout his talk show’s chaotic run.
Speaking to Entertainment Tonight, Andy recalled a 2013 episode of his Bravo talk show with Oprah Winfrey, during which he speculated about her sexuality by cheekily asking if she’d ever slept with a woman.
“That’s probably one of my few regrets,” he told ET last week, remembering that the interview had been going smoothly until he decided to ask if she’d ever “taken a dip in the lady pond.”
“It meant so much to me that Oprah Winfrey did the show,” he said. “It’s gone brilliantly, and I turn around and ask her if she’s ever had sex with a woman. I mean, couldn’t I leave it alone?”
Bravo / NBCU Photo Bank / NBCUniversal via Getty ImagesIn the episode, Oprah replies, “No, no, I have not. Thank you.” And it wasn’t until a few days later that Andy heard from Gayle King that the media mogul wasn’t entirely sure what the question meant.
“Gayle King told me later that week that Oprah didn’t know what I meant by ‘the lady pond.’ I thought I explained it pretty well there, but listen, I was so grateful that Oprah did the show, and I still am,” he said, clarifying that “it was not awkward” between them after they stopped filming.
“That remains, I think, my favorite episode,” Andy added.
Bravo / NBCU Photo Bank / NBCUniversal via Getty ImagesWWHL has brought fans some incredible celebrity moments over the years, from shady confessions to iconic reenactments. While speaking to ET, Andy said the “secret to the success” of the show is “spontaneity, authenticity, fun, humor,” and the fact that he’s never quite sure “what’s gonna happen” on the night.
“People let their guard down here. It’s also live, we’re on at night, we serve alcohol,” he said, noting that the “small” size of the studio can be “deceptive” for guests. “People don’t realize they’re actually on television.”
