Errors, gaffes, and slip-ups are to be expected when working in Hollywood, but not all bloopers are created equal. Andy Cohen, creator of the Real Housewives franchise, admitted that one of his most unforgettable mishaps also involved one of the most influential women in TV history: Oprah Winfrey. After an excellent interview, everything went sideways due to one question, which relates to a long-standing rumor involving her best friend, Gayle King.
During a Fan Fest week episode of TODAY, Andy Cohen asked his peers whether or not they had ever had an unforgettable "oops" moment on set. After each anchor shared their personal misstep, the Watch What Happens Live! host revealed his moment included Oprah. After an above average formal sit down with the iconic former talk show host, Cohen inquired about her prior personal relations. The energy quickly changed, as he revealed how she responded:
I was doing a great interview with Oprah and the show was about to end, and I, idiot that I am, turned to her and I was like ‘Have you ever swam in the lady pond?’ She was like ‘Uhhh.’ She goes, ‘No.’ And then Gayle said she didn’t get the question.
Oof, that’s quite a doozy. Sure, plenty of people from Oscar winners to AGT participants experience bloopers, but it's easy to understand why the New Year's Eve Live co-host’s experience with Oprah Winfrey has stuck with him. It’s one thing to have a personal flub televised; it’s a whole other experience when it directly pertains to Oprah. And beyond all of that, to ask her about something that has shadowed her long-time friendship with King puts an awkward cherry on top.
Naturally, Cohen followed up quickly after the matter stating his regret and apologies, but clearly the interaction still haunts him. I can only assume he’s living through some triggers since he re-confessed his feelings about it amid the 2025 TV schedule. Or perhaps he’s made enough peace with it to at least share it as an example of where the line is with an interviewee.
But as mentioned, a fumble on set or in real time is pretty commonplace. It even happens to other pros in situations like when Jenna Bush Hager cursed live on air and Carson Daly mispronounced Leonardo DiCaprio’s name. At the end of the day, we’re all human and things going awry is inevitable. Most gaffes just don’t make it onto screens for millions of people to see! As for Andy Cohen’s bold question to Oprah, it’ll float around in blooper infamy.
If you'd like to watch whole episodes, catch TODAY weekdays starting at 7 a.m. EST or stream past episodes with a Peacock subscription. You can also catch Cohen’s Watch What Happens Live! on Bravo, weekday evenings at 10 p.m. EST.
