“Couldn’t I Leave It Alone?”: Andy Cohen Revealed The One Question He “Regrets” Asking Oprah Winfrey In 2013

    “It meant so much to me that Oprah Winfrey did the show... I mean, couldn’t I leave it alone?”

    As he celebrates 15 years of Watch What Happens Live, Andy Cohen has revealed a “few regrets” throughout his talk show’s chaotic run.

    Andy Cohen is sitting on a talk show set of "Watch What Happens Live" celebrating its 15th anniversary

    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.

    Oprah Winfrey poses on the red carpet in an off-the-shoulder, fitted purple dress, adorned with delicate patterns. She accessorizes with glasses and earrings

    “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.”

    Andy Cohen and Oprah Winfrey chat and laugh on a brightly decorated talk show set on "Watch What Happens Live". Andy is in a suit, Oprah wears a stylish black outfit

    In 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.

    Andy Cohen and Oprah Winfrey high-fiving each other on a talk show set with bookshelves and colorful decorations in the background

    “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.

    Oprah Winfrey in a stylish black outfit and Andy Cohen in a dark suit with a yellow tie smiling on the set of "Watch What Happens Live."

    WWHL 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.

    Andy Cohen is smiling, seated in an indoor setting, wearing a light-colored suit jacket, a blue dress shirt, and a patterned tie

    “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.”

    Andy Cohen, Martha Stewart, and another person perform a drinking skit on "Andy Cohen's Watch What Happens Live" set
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