David Letterman Proposed To Dolly Parton During An Interview Despite Her Marriage To Carl Dean

Dolly Parton had been married for years but that didn’t stop David Letterman from asking her to marry him.

Highlights

David Letterman was infatuated with Dolly Parton’s looks and personality during her appearance on his show in 1987.
Letterman made flirtatious remarks to Parton and even asked her to marry him, despite her being married at the time.
Dolly Parton has been happily married to Carl Dean since 1966.

During David Letterman’s career, he interviewed most of the top music stars. In most cases, Letterman didn’t seem fazed by sharing the stage with music legends, which makes sense, since he was rich and successful enough to enjoy an incredible lifestyle.

Similar to Letterman, music supertsar Dolly Partonbecame extremely rich and famous. However, it wasn’t Parton’s riches that Letterman was struck by. Instead, Letterman clearly couldn’t get enough of Parton’s personality and looks which is why he asked her to marry him.

Why Did David Letterman Ask Dolly Parton To Marry Him?

Throughout Dolly Parton’s time in the public eye, she has always been known for her flashy fashion choices. While Parton’s family hated the way she dressed, David Letterman clearly enjoyed the way the country legend looked.

When Parton appeared on Late Night with David Letterman in 1987, she came out wearing a typically eye-catching outfit. Mostly made up of black clothing that looked pretty skin-tight, Parton’s outfit also featured shiny silver highlights.

Of course, Parton was also sporting her trademark large hair that always made her stand out. Between her clothes, makeup, and hair, it seemed like Letterman was instantly taken with Parton when she walked out onstage.

Instead of simply greeting Parton as he normally did with his guests, Letterman kissed the singer’s hand and pulled her in close to his side. With his hand around Parton’s waist, it looked as if Letterman was showing off her looks to the camera and studio audience. Letterman then proceeded to comment on how he and Parton looked like as a pair at that moment.

“I think we look good together. Don’t you think we look nice together? We should work together. We’ll go out and do shows together.”

Once Letterman removed his hand from Parton’s waist, the two of them sat down. However, Letterman almost instantly said something that could have indicated an attraction to Parton or could have been entirely innocent. “Boy, you smell great.”

What awards has Dollywood won according to Dollywood.com?

Tripadvisor’s #1 Theme Park in the United States
Ticket Awards for Best Kids’ Area
Ticket Awards for Best Christmas Event
Ticket Awards for Best Guest Experience

From there, the pair then proceeded to have a fairly typical interview for several minutes. Letterman asked Parton about Dollywood, the theme park the country singer had recently bought and begun running at the time of the interview.

At the end of Letterman and Parton’s discussion about Dollywood, the country singer asked the host to come to her theme park. As Parton pitched Letterman on coming to Dollywood and maybe even filming part of his show there, she said something he easily could have been insulted by.

“I want you to come down sometime and, cause I know you do fun stuff on your show and what you like. It would be a good place for you to come and act stupid and have fun doing it.”

When Letterman and his studio audience had a big reaction to Parton’s comments, she tried to clarify what she meant. “I didn’t mean it bad. I meant fun stuff.”

Throughout David Letterman’s career, he has dealt with many celebrities taking verbal shots at him. In most of those cases, Letterman has used his infamously sharp tongue to unleash a savage comeback at those guests.

When Dolly Parton said something to David Letterman that he could have been insulted by, he didn’t have a witty retort. On top of that, Letterman didn’t seem to have much interest in Parton’s clarification. Instead, Letterman’s only response was to ask Parton to become his wife.

“Please, please marry me. Please. Will you consider it?”

After Parton stated she would consider Letterman’s request, the host asked her a follow-up question. “Are you married now?” In a truly hilarious moment, Parton confirmed she was married at the time which the studio audience laughed uproariously at. At this moment, Letterman’s trademark wit seemed to come back to him.

“You’re married now, but yet, you’re gonna consider marrying me? Well, don’t expect to treat me that way if we get married.”

Who Have Dolly Parton And David Letterman Been Married To?

When Dolly Parton told David Letterman she was married during their 1987 interview, it was far from a new marriage for the country singer. Instead, Parton has been married since the ’60s, and she seems to be very happy from all reports.

After Dolly Parton and Carl Dean got married in 1966, they have been together ever since. Furthermore, there has never even been a hint of a suggestion that Parton or her husband have been romantically interested in anyone else. In 2022, Parton spoke to ET Canada and revealed two key factors that have allowed her marriage to last. First off, Parton credited each of them having their own space.

“I like it when people say, ‘How did it last so long?’ I say, ‘It’s stay going. You know, there’s a lot to be said about that. So, we’re not in each other’s face all the time. He’s not in the business so we have different interests, but yet we have the things we love to do together. So it was meant to be, I think. He was the one I was supposed to have and vice versa.”

Secondly, Parton credited her lasting marriage to having a similar sense of humor as her husband.

“We both have a warped sense of humor. And I think humor, honestly, is one of the best things when you’re married like that. Even if you have a problem, if you have a great sense of humor, if you say something you can’t take back [you] usually have some crazy way of getting out of it.”

Unlike Parton, Letterman’s love life has been a lot more tumultuous. After all, Letterman infamously engaged in affairs and someone tried to blackmail him over them. Much to the shock of the blackmailer, Letterman decided to go public with his affairs instead of being extorted.

Who has David Letterman been involved with according to Whos Dated Who?

David Letterman began dating Regina Lasko in 1986
David Letterman and Regina Lasko got engaged in 2001
David Letterman and Regina Lasko have been married since 19th Mar 2009
David Letterman and Stephanie Birkitt had an affair between 2001 and 2003
David Letterman had a fling with Terri Garr in 1990
David Letterman dated Bonnie Hunt

Even though Letterman hasn’t always been faithful, he has been in a relationship with a woman named Regina Lasko for decades. After reportedly starting to date in 1986, Letterman and Lasko’s son was born in 2003 and they got married in 2009.