Andy Cohen's Biggest Regret on 'WWHL!' Involves None Other Than Oprah: "Couldn't I Leave It Alone?"

Andy Cohen has established himself as one of the most popular television hosts, with his show Watch What Happens Live! loved for its controversial content. In a recent interview with Entertainment Tonight, Cohen celebrated a significant milestone—15 years as the host of the late-night Bravo show. Reflecting on his journey, Cohen shared an instance from when Oprah Winfrey graced his show and admitted he regretted asking her a particular question, HuffPost reported.

Cohen stated, "This was a huge moment for me and the show. I'm such a fan of Oprah." However, Cohen couldn't resist asking Winfrey if she had ever 'taken a dip in the lady pond.' He said, "That's probably one of my few regrets... 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 sex with a woman. I mean, couldn't I leave it alone?" At the time, Winfrey said, "No, no I have not. Thank you," as reported by Entertainment Tonight.

The Bravo star noted that Winfrey was 'super cool' throughout the interview. However, he later learned from her friend Gayle King that Winfrey might not have grasped the meaning of his question. Cohen said, "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. That remains, I think, my favorite episode." In 2018 too, he had expressed, “The second after I said it, I kind of regretted it.”

Subsequently, getting nostalgic, Cohen opined, "The secret to the success of Watch What Happens Live, I think, is spontaneity, authenticity, fun, humor, me going there, and people never knowing what's gonna happen. People let their guard down here. It's also live, we're on at night, and we serve alcohol." He added, "It's so small in here that it's deceptive, like, people don't realize they're actually on television."

Speaking about his relationship with popular host, Anderson Cooper, Cohen said, "The friendship I have with Anderson means a lot. We've gotten so much closer over the past 15 years." He added, "We've been on tour together, we co-host New Year's Eve together, we've been through a lot, and being dads together has been a great joy in our lives."

Cohen also elaborated on how becoming a dad changed him: "Being a dad has changed how I approach work, too. I come, I do my thing, I go home to the kids and I love bringing them here." He continued, "I used to go out every night until all hours after the show, and now I stay home. I go home and kiss my kids goodnight while they're sleeping and I can't wait to see them in the morning. My life has totally changed and I wouldn't have imagined this for myself 15 years ago."