Talk shows are usually all about fun and honest chats, but sometimes things can get really awkward! That’s what happened when Andy Cohen, the host of a popular show, interviewed media icon Oprah Winfrey in 2013. Things got a little uncomfortable, and he later regretted asking a question that left Winfrey a little speechless.

Watch What Happens Live With Andy Cohen
Watch What Happens Live With Andy Cohen (Credits: Bravo Media)

Cohen is known for his witty banter and entertaining conversations. He keeps everyone laughing with his charming humor and playful style. However, he recently opened up about that particular moment that still makes him cringe.

Andy Cohen Admits Regret Over Question to Oprah Winfrey

Oprah Winfrey (Credits: X/@oprahwinfrey)
Oprah Winfrey (Credits: X/@Oprah)

Many of us have experienced that awkward moment of saying something we instantly wish we could take back. For talk show host Andy Cohen, that moment came during a 2013 interview with media mogul Oprah Winfrey.

Cohen recently opened up about his regret in an interview with Entertainment Tonight, revealing a question he posed to Winfrey that ended up going awry. The question, which indirectly inquired if the actress has had a s*xual experience with another woman, left both of them feeling a bit awkward for a moment. “That’s probably one of my few regrets,” the 56-year-old admitted.

He was excited to have the 70-year-old on the show, but soon realized the conversation had taken an uncomfortable turn. Winfrey is known for keeping her personal life private, and Cohen’s question moved away from the usual light-hearted chat. The late-night talk show said:

It meant so much to me that Oprah Winfrey did the show. It’s gone brilliantly and I turn around and ask her if she’s ever had s*x with a woman. I mean, couldn’t I leave it alone? 

In response, the star of The Butler looked directly at Cohen and replied, “No, I have not. Thank you.” During the already awkward interview, the writer of The Daddy Diaries: The Year I Grew Up confessed that Winfrey might not have understood his question.

Andy Cohen is Still Grateful for Oprah Winfrey Interview

Andy Cohen and Oprah Winfrey on Watch What Happens Live With Andy Cohen (Credits: Bravo Media)
Andy Cohen and Oprah Winfrey on Watch What Happens Live With Andy Cohen (Credits: Bravo Media)

Andy Cohen asked Oprah Winfrey the question using a fancy term, referring to a “lady pond,” but it seems the Children of Anguish and Anarchy author didn’t know what he was talking about. The executive producer of The Real Housewives stated in the same interview:

Gayle King told me later that week that Oprah didn’t know what I meant by ‘the lady pond. 

Even though the question flopped, Cohen chooses to focus on the positive side of his interview with Winfrey. He continued, “I was so grateful that Oprah did the show and I still am.”

Cohen went on to say that despite the awkwardness, the interview with Winfrey is still his favorite episode of Watch What Happens Live! Interestingly, Cohen celebrated the 15th anniversary of WWHL this month in June.

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