Watch What Happens Live Host Andy Cohen Regrets His Question To Oprah Winfrey

When people talk about the most successful talk show hosts of all time, Oprah Winfrey has to top the list since she has a huge fortune to spend. The reason for that is that Oprah has loads of fans who love her so much that they want to know things like what her relationship with Ellen DeGeneres was like.

For that reason, it was a big deal for Andy Cohen when Oprah appeared on Watch What Happens Live. Since Andy is open about things like his opinion of "cancel culture" and when he felt snubbed, it shouldn't surprise anyone that he admitted how he felt about his Oprah interview. Sadly for Andy, he admitted that he regretted a question he asked Oprah during the interview.

Andy Cohen Regretted Asking Oprah Winfrey An Awkward Question

In the modern world, it sometimes seems like people throw around words like "legend" and "icon" too freely. After all, it can seem like the only thing someone needs to achieve to be called one of those words is be famous for many years. However, there are some celebrities who absolutely deserve to be called legendary and iconic. One person who is a perfect example of the kind of celebrity who should be called iconic is Oprah Winfrey.

Since Oprah has accomplished so much and affected so many people, getting to interview her seems like it would be a dream come true. Unfortunately for Andy Cohen, however, he got to interview Oprah and walked away from their interaction with a big regret.

In August 2013, Andy Cohen welcomed Oprah Winfrey to his celebrated talk show, Watch What Happens Live with Andy Cohen.

As is always the case with Andy's talk show, the host and his guest then proceeded to discuss a myriad of different topics.

Many years later, in July 2024, Andy was speaking to Entertainment Tonight about his career.

In June 2024, Andy Cohen's career reached an incredible milestone. During that month, Bravo aired a special titled Watch What Happens Live’s 15th Anniversary Special to celebrate how long Andy's talk show had been successful.

While talking to the host, for a video which can be seen on Entertainment Tonight's YouTube channel, the outlet played Andy memorable moments from his career. Andy would then go on to reflect on those moments from his past while addressing the camera.

While many of the clips that ET played for Andy made him happy, one of the clips that involved Oprah Winfrey filled him with regret.

In the clip that was shown to Andy, he could be seen asking Oprah if she'd ever been intimately involved with a woman.

According to an April 2024 People article, Oprah Winfrey has been in a relationship with Stedman Graham since 1986. The same article revealed that Oprah and Stedman got engaged in 1992 but called off their plans to get married in 1993. Still together ever since, Oprah once stated that she believes her relationship with Stedman wouldn't have lasted if they got married.

While asking Oprah about her intimate past, Andy phrased that question in an interesting way.

[Have you] ever taken a dip in the lady pond?

In response to Andy's question, Oprah spoke with a tone of voice that made it seem like she didn't really appreciate that question.

Oprah also told Andy that she had never been involved with a woman in that way.

No. I have not. No. Thank you.

After the clip was shown, the video cuts to Andy reacting to it. Andy begins by expressing that although he usually avoids regrets, he is bothered by that moment with Oprah. Andy also explained to ET what it was about that moment that bothered him so much.

"That's probably one of my few regrets. It meant so much to me that Oprah Winfrey did the show. And we were running out of time. And genius that I am chose... You know, we're about to end 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?"

Andy also went to give Entertainment Tonight some behind the scenes information about that awkward moment. According to Andy, Oprah's close friend, Gayle King, later talked to him about how he initially worded the question.

In March 2024, the official Oprah Daily website published an article about Oprah Winfrey and Gayle King's much talked about friendship. That article revealed that Oprah and Gayle have been very close friends since the first night they met in 1976.

As Andy explained, Gayle told him that Oprah didn't know what he meant by, "taken in a dip in the lady pond".

"Now the way that I phrased it was, 'Have you ever swam in the lady pond?' Which was something that I would say a lot at the time. Gayle King told me later that week that Oprah didn't know what I meant by 'the lady pond'."

Fortunately for Andy, however, his interview with Oprah wasn't all bad.

Andy Cohen Still Loved Most Of His Oprah Winfrey Interview

When Andy Cohen interviewed Oprah Winfrey in August 2013, it was a huge deal for the hosts and people who were fans of both stars. As a result, Today published an article at that time focused on some of the most remarkable moments from Andy and Oprah's Watch What Happens Live interview.

That article highlighted several fascinating moments from Oprah's Watch What Happens Live interview. For example, Oprah told Andy that she didn't mind when Terrence Howard once commented that she had a large chest. The reason for that, as Oprah explained to Andy, was that she felt that what Terrence said was true.

Today's article also revealed that when a fan asked Andy how Oprah smelled, he ultimately stated, "The scent of Oprah just smells perfect." If that wasn't enough, the article also focused on the funny and pained reactions that Oprah had when Andy showed photos of her different hairstyles over the years.

Given the positive parts of Andy and Oprah's interview, something he told Entertainment Tonight makes a lot of sense. After telling ET in the aforementioned YouTube video that he regretted asking Oprah that one question, Andy revealed how much he loved interviewing her.

"I was so grateful that Oprah did the show and I still am. That remains, I think, my favorite episode... She was cool. It was not awkward after the show. She was super cool."

While it is too bad that Andy regretted that one question, it is fantastic to know Andy still loved talking to Oprah.