How David Letterman's Cheating Scandal Rocked His Marriage

David Letterman was known for his acerbic sense of humor during his time as host of his eponymous nighttime show, but the scandal that unfolded in 2009 and affected his marriage was anything but funny. Letterman and Regina Lasko started dating in the mid-1980s but didn't get married until the same year his cheating was outed. Although the funnyman interviewed countless celebrities with probing questions on "The David Letterman Show," he maintained a pretty private life and didn't share a lot of details with the public. As reported by several media outlets, Letterman and Lasko privately got married in March 2009 at a courthouse in Montana. They were accompanied by their then-five-year-old son Harry and friends Genevieve and Lee Barhaugh. Letterman addressed his quiet marriage on his show by telling the audience, per People, "I had avoided getting married pretty good for, like, 23 years. People say, 'Geez, Dave, you were together so long. Does it feel any different?' And I say, 'Yeah. It does.'"

The following October, Letterman dropped another piece of shocking news on his show. "This morning, I did something I've never done in my life. I had to go downtown and testify before a grand jury," he revealed, per ABC News. He admitted to having had sex with women who worked for him and was caught in an extortion attempt of $2 million. Although the audience was stunned, no one could have been more horrified than his wife, and Letterman later gave her the public apology that she deserved.

Cheating scandals are never easy to swallow, particularly when you're in the public eye. While Regina Lasko had maintained a life out of the spotlight, she inadvertently got caught up in her famous husband's impropriety. After admitting to his multiple sexual relations with staff members, David Letterman stated on his show the following week that Lasko was "horribly hurt" by his actions, CBS reported. "Let me tell you, folks, I got my work cut out for me," he told the audience. He added, "I just wasn't thinking ahead. My thanks to the staff for, once again, putting up with something stupid I've gotten myself involved in."

Although Letterman — who clearly has a shady side — didn't share details, more information came out later. A former female assistant named Stephanie Birkitt was one of the several women he had an affair with, per CBS. Birkitt was already in a relationship with her then-boyfriend CBS News producer Joe Halderman. After finding Birkitt's diary with details about her affair with Letterman, Halderman attempted to blackmail the television host out of $2 million. Letterman then reported the extortion and gave Halderman a fake check, which he tried to deposit. Halderman was consequently arrested. While many would have understood if Lasko had walked away from her marriage, she ended up staying with Letterman, but it took a lot to save their relationship.

Three years after the cheating scandal — which would become one of David Letterman's most controversial moments — unfolded, he was still trying to get back into Regina Lasko's good graces. In an interview with Oprah Winfrey, per YouTube, when asked if he thought his wife would stick by him, he replied, "Don't know. Well, it wasn't certain at the time." He revealed that he was in the doghouse, sharing, "I slept a wide variety of places." Letterman added, "I'm still trying to fix it." Elsewhere in the talk, he stated (via YouTube), "I have no one to blame but myself. And now, I feel better about myself, my relationship with my wife is never better and it's just because I want to be the person I always thought I was and probably was pretending I was."

Over a decade later, it seems that Letterman and Lasko are doing well. The former talk show host shared on "The Late Show with Stephen Colbert" in November 2023 that he and his wife are empty nesters and spend a lot of time running errands together. He also hasn't lost his sense of humor over the years. Letterman joked, "When Harry left a year ago — he's a sophomore now — when he left, we decided we would do one of two things. My wife and I had a consult about this. One, we would either have another child ... or get a divorce. The paperwork, honestly, is about the same so either way, we are kind of stuck."