Andy Cohen Says Asking Oprah Winfrey If She’s Ever Taken a ‘Dip in the Lady Pond’ Is One of His ‘Regrets’

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Andy Cohen says he still cringes recalling a moment from an interview he did with Oprah Winfrey more than a decade ago.

In a new interview with Entertainment Tonight looking back at some of the highs and lows of his career, the TV host, 56, said one of his “few regrets” is asking Winfrey, now 70, if she’s ever “taken a dip in the lady pond” on a 2013 episode of his Watch What Happens Live talk show.

Cohen was asking her to reveal if she’d ever had a sexual encounter with a woman.

That’s probably one of my few regrets,” he told ET of his choice to ask Winfrey the personal question, which he told her at the time was a “classic” query on the Bravo show.

As seen in a video clip of the moment shared by ET, in response, the Color Purple Star stared at Cohen and said very directly, “No, I have not. Thank you.”

“It meant so much to me that Oprah Winfrey did the show,” Cohen told ET. “It’s gone brilliantly and I turn around and ask her if she’s every had sex with a woman. I mean, couldn’t I leave it alone?” 

He said that after he asked the question and the cameras had stopped rolling, Winfrey did not make him feel awkward for prying into her sex life.

However, he later got some inside information from the media mogul’s best friend Gayle King about how Winfrey felt in the moment.

“Gayle King told me later that week that Oprah didn’t know what I meant by ‘the lady pond,’ ” he said. “I thought I explained it pretty well there, but listen, I was so grateful that Oprah did the show and I still am.

Despite his overstep, Cohen has fond memories of his interview with Winfrey. “That remains, I think, my favorite episode[of WWHL],” he said.

ET was interviewing Cohen to celebrate the 15th anniversary of WWHL, which is in June.

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