The Sad Truth About David Letterman's Relationship With His Wife

When longtime late night TV host David Letterman retired in 2015, after more than three decades on the air, his wife, Regina Lasko, and their son, Harry Joseph Letterman, appeared in the final episode, according to IMDb. This presented Letterman and his family as a strong and cohesive unit, and after more than 30 years with Lasko at the time of this writing, that may very well be the case. As anyone who has followed the acclaimed comedian and TV personality knows, though, Letterman's relationship with Lasko has had its fair share of ups and downs.

Regina Lasko is not David Letterman's first wife, as Biography explains. Letterman and his first wife, Michelle Cook, were college sweethearts who married in 1968, and they divorced about nine years later. Letterman was in another relationship with a woman named Merrill Markoe when he met Lasko in 1986. Markoe was a head writer on Letterman's show. These poor professional boundaries on Letterman's part would come back to haunt his relationship with Lasko when they finally married in Montana in 2009, after more than two decades spent as a couple (via Biography).

Lasko and Letterman's son was subject to a kidnapping plot

At the point that David Letterman and Regina Lasko married, their son, Harry Joseph was just six years old. Both Lasko — who has worked behind the scenes in the entertainment business for Letterman's show as well as "Saturday Night Live" — and the TV host had their son later in life, per The Things. When Harry Joseph was just two years old, the first big test of Letterman and Lasko's relationship came about.

In 2005, a Montana man named Kelly Allen Frank threatened to kidnap their son, as well as the young boy's nanny, demanding a $5 million ransom. Frank worked on the Montana ranch owned by Letterman and Lasko, as ABC News reports. The worst nightmare of every new parent never came to pass, and Frank was arrested and sent to jail. Frank broke out in 2007, and as a result, he was given 10 more years in prison. He was released in 2018 (via The Things). Harry Joseph Letterman was unharmed.

David Letterman cheated on Lasko

The 2005 kidnapping attempt on Harry Joseph was just the first of two major incidents that would strain David Letterman's relationship with his wife, Regina Lasko. In 2009, the same year Lasko and Letterman were married, Letterman was blackmailed by a man who at that time was dating Stephanie Birkitt, a woman who Letterman slept with while she was an intern on his show. The man demanded $2 million from the talk show host or the infidelity would be revealed to the public, according to Vice Magazine.

Letterman admitted the affair on the air, and it was subsequently revealed that Birkitt was not the only employee with whom he had cheated on Lasko. The man attempting to blackmail Letterman was also arrested (per Vice). During this period, Letterman spoke to Oprah Winfrey about this tough time in his marriage.  "I have no one to blame but myself," for the sex scandal, Letterman said, adding that Lasko had forgiven him, but the same couldn't be said for Letterman forgiving himself. "I don't have that luxury," Letterman said (via US Magazine).

Letterman and Lasko, a happy ending

Cheating and attempted child abduction aside, David Letterman and his wife Regina Lasko have remained together and seem to have worked through their differences and setbacks, endured both before and after they married. Letterman and Lasko enjoy doing  attending classical music concerts (via The Things), and they were even spotted on the Caribbean island of St. Barts, celebrating the New Year's holiday in 2020, per Daily Mail

Part of what makes the relationship work, according to Letterman, is his willingness to take full responsibility for his past infidelities. "I think if you're going to have a flow chart of the responsibility for this circumstance, for this sex scandal, my name is at the top... I'm taking responsibility for it, trying to atone for it," the TV host told Oprah Winfrey. "My life is fun and full of joy now," he said. "I only pretended it before."