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David Letterman Affair: What Happened in the Cheating Scandal?

David Letterman
David Letterman the famous TV show host of the Late Night Show

In October 2009, David Letterman told his audience about confessing cheating on his wife with two other women who worked with him on his show – The Late Show. The affair of Letterman came to light in the press after he confessed on the Late Show. He had been sleeping with Stephanie Birkitt, a 34-year-old intern; she had gone from being an intern to his personal assistant.

She had appeared in many segments of the Late Night Show, including as a correspondent at the Olympics. The other woman that David slept with was Holly Hester, and she dated Letterman when she was also an intern on the Late Show and a student at NYU. 

David Letterman Confesses Cheating On His Wife: 

In October 2009, David Letterman told his audience about an incident. He said that a few weeks earlier, he got into his car early in the morning and found a mysterious parcel in his backseat. Inside the parcel was a letter that said- “I know you have done some terrible things, and I can prove that.” With the letter was the stuff containing information which proved that he had done those terrible things, Letterman told on air. 

David Letterman

David Letterman with his wife Regina Lasko at the Kennedy Centre

A peal of nervous laughteroom as the audience was unprepared for this. At first, Letterman did not address the “terrible things.” He said he called his lawyer and told him the blackmailer had demanded $ 2 million for 2 million quiet. After that, he and his lawyer contacted and reported the matter to the Manhattan District Attorney’s Office.

The blackmailer was given a phony check of $ 2 million and was caught only hours before that day’s “Late Show” taping. The audience clapped and laughed at this monologue which he prepped with jokes and descriptions. At first, the whole thing felt like a stand-up routine until Letterman finally revealed the “terrible things” his blackmailer mentioned. 

“The “terrible thing” was that I have slept with women who work for me on the show,” he said, “the studio went silent. He continued, “Now my answer to that is- Yes, I have. Would it be embarrassing if this was made public? Probably it would, especially for women!” He managed to make a joke, and the crowd laughed and applauded. 

This was all that Letterman said on the matter, but over the next few days, details came to light in the press about him cheating on his wife with 2 other women. Letterman was married to Regina Lasko when he confessed to having slept with women who worked for him. The two met when Regina was a production staffer on the Late Night with David Letterman show. 

Also read: When Wi, When Is A Joke Pete Davidson 2022 Special Release?

David Letterman Apologizes To Staff And His Wife:

The day after Letterman made his confconfessedShow, he spoke about his infidelities on-air and apologized to his wife and staff. He said that his wife is horrible, hurt, horribly behavior. 

The response to Letterman’s confessions was a big collective shrug. On “The View,” Barbara Walters praised him for coming clean and called him an attractive man. She also emphasized that he was not accused of sexual harassment. The New York Times writer Maureen Dow also dismissed the notion that Letterman did not pressure any woman to get involved with him. 

David Letterman

David Letterman confesses cheating on wife on air

Also read: Jerry Seinfeld’s Dating History: The Comedian’s Relationships So Far

Stephanie Birkitt, who had an affair with Letterman, was promoted from an intern to his assistant and became a regular on air-talent. According to the New York Magazine, Birkitt and her relationship with Letterman was an open secret at that time. The blackmailer was her boyfriend, Joe Halderman. 

Nell Scovell, who wrote for Late Night in the 1990s in the year 2009, wrote in Vanity Fair that Letterman’s engagement with his female staff, which apparently was not limited to just Hester and Birkitt, made working for him uncomfortable. So much uncomfortable that she walked away from her dream job. She has written a full article in Vanity Fair expressing her views about the matter and on Letterman’s behavior. 

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Hi! I'm Swarnjeet Kaur, from Jodhpur AKA Suncity and I write content on lifestyle. Hope all you guys like my articles!

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