David Letterman couldn't resist proposing to Dolly Parton but it didn't go as planned: "Don't expect..."
Dolly Parton is the darling of American country music who has captivated fans with her angelic voice for over five decades. The 79-year-old singer recently had a major personal setback when her husband of 60 years, Carl Thomas Dean, passed away on March 3, 2025. While Parton was surely left heartbroken, she never shied away from flaunting her love for Dean. Despite this, Parton had many admirers, and one of them was David Letterman. The legendary talk show host's affection for Parton was visible when he openly proposed to her.
In 1987, Parton made a memorable appearance on 'Late Night with David Letterman,' where she wore a striking black, skin-tight outfit with shiny silver accents. Her trademark voluminous hair completed the bold look, leaving Letterman visibly impressed by her presence as she walked onstage. When Parton appeared on the talk show, Letterman greeted her differently than usual, kissing her hand and pulling her close with his hand around her waist, as per The Things. It appeared as though Letterman was showcasing her appearance to the camera and audience. He then commented on how they looked as a pair at that moment.
Letterman remarked, "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 they sat down, Letterman quickly added, "Boy, you smell great." During the interview, Letterman and Parton discussed Dollywood, the theme park that she at the time had purchased. At the end of their conversation about the park, Parton invited Letterman to visit, even suggesting he film part of his show there.
Parton said, "I want you to come down sometime and, because 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 Parton told Letterman that he could come to Dollywood and "act stupid and have fun doing it," the audience reacted strongly, prompting Parton to clarify, saying, "I didn't mean it bad. I meant fun stuff." However, Letterman didn’t respond with a witty remark or acknowledge her clarification. Instead, he immediately asked, "Please, please marry me. Please. Will you consider it?"
After Parton agreed to consider his marriage proposal, Latterman was left regretting it when he discovered Parton was already enjoying marital bliss. Latterman asks Parton, "Are you married now?" Parton confirmed she was, prompting laughter from the studio audience. In response, Letterman regained his trademark wit, quipping, "You're married now, but yet, you're going to consider marrying me? Well, don't expect to treat me that way if we get married."
Notably, Parton, in an interview with W Magazine, shared about her talk show host crush, and unfortunately, Letterman was not the one. The 'Jolene' singer admitted to having a crush on Jimmy Fallon, as per Taste of Country. She said, "Well, I have a crush on Jimmy Fallon... I think he is precious. He's so funny. We get along so well," highlighting her admiration for the late-night host.