Regina Lasko and David Letterman’s Relationship Timeline

David Letterman has been with his wife Regina Lasko for 36 years, and they share a son, Harry Joseph Letterman. The family of three was once spotted together during an outing in early 2020.

Comedian, TV host, producer, and writer David Letterman and his wife Regina Lasko, who he has been with for nearly four decades, were in the sunny St. Barts in January 2020. The couple and their teen son Harry Joseph celebrated the New Year together while looking relaxed and casual. David stood out in yellow shorts, a white t-shirt, and bright orange sneakers.

His wife, Regina, looked stylish in a lightweight white top and khaki shorts. She completed her look with stunning sandals that matched her beautiful handbag. The husband and wife also accessorized with dark sunglasses. Their son Harry, who looked nearly as tall as his dad, also stood out in an orange t-shirt, dark-colored shorts, and black and white sandals.

Regina Lasko and David Letterman attend the 2017 Museum Gala on November, 30, 2017 in New York. | Source: Getty Images

David is one of the most recognized male figures in the entertainment industry who has been a talk show host for over three decades. The 75-year-old has interviewed many Hollywood stars and prominent people over the years, including Barack Obama, the former president of the United States, on his series on Netflix, “My Next Guest Needs No Introduction.”

His reputation has, however, been tarnished by videos of him behaving inappropriately towards female guests. For this reason, many are surprised that he has stayed with his wife the whole time. David Letterman’s wife has remained on her husband’s side through all the ups and downs. Regina, born November 20, 1960, pursued a career in the entertainment industry from an early age.

She has faced, and overcome, a lot in her marriage, including blackmail, a kidnapping plot, and obscene rumors. Here’s what we found out about David Letterman and Regina Lasko’s 36-year marriage.

1986: DAVID LETTERMAN MET REGINA LASKO

David Letterman and Regina Lasko met in 1986 and fell in love in no time. However, David was already in a longtime relationship with someone else, the head writer on “Late Night with David Letterman,” Merrill Markoe. Even though the talk show host was dating Regina, he continued his relationship with Merrill, whom he was staying with, but ended things with her in 1988.

1987: REGINA STARTED WORKING ON HIS SHOW

Just like how David Letterman’s ex-girlfriend Merrill Markoe worked with him on the show, Regina Lasko pursued a career in the entertainment industry. In fact, she also started working with David when they became a couple. She has played an integral part in the teams behind the scenes of various shows David has worked on.

Regina is currently a production manager; she joined the industry in 1987 after meeting David and worked with him on “Late Night with David Letterman” until 1989. Another show that David Letterman’s wife has worked on behind the scenes is “Saturday Night Live.”

David Letterman holds a photo of his new son, Harry Joseph Letterman on ‘The Late Show with David Letterman’ on November 4, 2003 on the CBS Television Network. I Source: Getty Images

2003: COUPLE WELCOMED A SON

Regina Lasko gave birth to her son Harry Joseph in 2003 at the age of 43. Her husband, David, who was 56 years old at the time, became a father for the first time. It has become common among celebs, and everyone in general, to have children later in life. Their son Harry turned 18 in 2021, and his main focus was reportedly his schooling.

2005: THEIR SON WAS ALMOST KIDNAPPED

While enjoying the excitement of becoming new parents, David Letterman and Regina Lasko’s only child was almost kidnapped in 2005. The couple had to face the one thing that most parents fear, which is losing their child when someone plotted to kidnap Harry, who was a toddler at the time.

A man who reportedly worked as a painter on the couple’s ranch in Montana, Kelly Allen Frank, threatened to kidnap their son Harry and the boy’s nanny. Frank also planned to demand a ransom of $5 million.

David Letterman with his son Harry Joseph at the 20th Annual Mark Twain Prize for American Humor in Washington, DC, on October 22, 2017. I Source: Getty Images

Thankfully, Frank’s plans never came to pass, and Harry was not harmed as Frank was arrested and jailed before kidnapping him. He later escaped prison in 2007, leading him to get an extra 10 years in jail. Frank was eventually released from prison in 2018.

2009: DAVID AND REGINA FINALLY MARRIED

David and Regina may have met way back in 1986, but they did not rush to get married right away and chose to enjoy each other’s company without the pressure of changing their relationship status.

It was only after the couple had already had a child together and had dated for 23 years that they decided to get married in 2009. They had a simple yet beautiful wedding ceremony in Choteau, Montana, with only a few friends in attendance.

2009: CHEATING SCANDAL

David and Regina may have been together for decades, but their relationship was still tested in various ways — one notable incident was a cheating scandal. In 2009, David admitted on air on his show that he had slept with women who work for him. The comedian expressed how grateful he was that his wife never left him after the scandal six years later.

The comedian also revealed that he had still not explained his infidelity to his son Harry. At the time, David further said about the situation:

“We’ll have to have a conversation about it. But not yet.”

2020: COUPLE IS STILL TOGETHER

The trials and tests the couple faced with the cheating scandal and their son almost getting kidnapped clearly weren’t enough to break the husband and wife’s strong relationship. David and Regina are going strong still and love going out together. They love attending classical concerts together and going on dates, with them being spotted in St. Barts on New Year in 2020, where they went on a date.

DAVID ABOUT HIS WIFE REGINA

As mentioned earlier, David only married Regina after dating her for 23 years. Many have wondered why the comedian took so long to marry his partner. In a previous interview, he had this to say about the matter:

“I had avoided getting married pretty good [sic] for, like, 23 years, and … honestly, whether this happened or not, I secretly felt that men who were married admired me like I was the last of the real gunslingers — you know what I’m saying?”

The adoring husband, who worked with his wife for years in the entertainment industry, was not shy to boast about how brilliant his other half was. Speaking of his exceptional wife, who he also says he has a lot of fun with, David said, “She’s very smart. She worked in broadcasting, so she knows everything I do here. And in addition to being a practical combination, we just have a lot of fun.”

David revealed how supportive his wife has been throughout the years and the funny moments they share as a family. He revealed:

“Harry and I have a lot of fun making fun of her, and she has a lot of fun pretending to be outraged. And I know she’s sick of all my jokes. But she has been excellent company and has readily played along with the nonsense and bizarre stuff that the family has done.”

David also expressed how grateful he is that he still has his family, and they are still together. He went on to say how he came very close to having the whole thing explode and losing it all. In an interview with Rolling Stone, David said his wife’s “not very athletic” and very terrible at skiing, but has made an effort to join her husband and son, who love skiing.

David Letterman and Regina Lasko have faced a lot of troubles in their relationship and might face more in the future. However, it’s inspiring that the couple has chosen to stick together no matter what.

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