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TV Host's Awkward Oprah Winfrey Interview Question Becomes Infamous Blooper
30 Oct
Summary
- Andy Cohen's unforgettable mishap during Oprah Winfrey interview
- Winfrey's response after Cohen asked about her friendship with Gayle King
- Cohen's regret and apologies following the awkward interaction
As of October 2025, TV personality Andy Cohen has recounted one of his most memorable blunders—an awkward interview with media mogul Oprah Winfrey. During a Fan Fest week episode of TODAY last month, Cohen shared that his unforgettable "oops" moment occurred after an otherwise excellent sit-down with the iconic former talk show host.
After the formal interview, Cohen inquired about Winfrey's long-standing friendship with her best friend, Gayle King. However, this question quickly changed the energy, as Winfrey responded in an unexpected way. Cohen immediately followed up with regret and apologies, but the interaction has clearly stuck with him as an infamous blooper in the entertainment industry.
While slip-ups are common in Hollywood, Cohen's experience with Winfrey stands out due to the high-profile nature of the individuals involved. Asking the media mogul about a personal matter related to her close friend puts an awkward spin on the situation. Even years later, the New Year's Eve Live co-host continues to reflect on this particular mishap, likely due to the triggers it has caused.
