Dolly Parton has taken a surprising turn in her new partnership with Khloé Kardashian. While their joint limited-edition jeans project made headlines in May, it’s the country icon’s behind-the-scenes mission that’s stirring buzz—playing cupid for the famously unlucky-in-love Kardashian sister.
Sources close to the duo revealed that the 72-year-old music legend was shocked to learn Khloé has not been on a date in three years. According to insiders, the Good American founder openly told Dolly that she’s been choosing to stay single since her last public breakup.
Dolly reportedly found Khloé’s dating drought hard to believe and immediately took it upon herself to change that. She believes Khloé deserves more than the heartbreak she endured in past relationships and has been actively talking to her about potential matches.
Reality star confesses dating pause on her podcast
On a recent episode of her podcast Khloé in Wonder Land, the 40-year-old reality star opened up about her decision to step away from dating. She shared that she hasn’t been on a single date in three years, explaining that it was intentional and part of her healing process.
Khloé admitted she chose to focus on her daughter and career, avoiding romantic relationships to protect her peace. That confession, sources say, struck a chord with Dolly.
The music icon, who was married to her late husband Carl Dean for nearly 62 years, couldn’t understand how someone as successful, beautiful and loving as Khloé remained single. Insiders say Dolly told friends she knows plenty of single men in the industry who would drop everything for a chance with her new collaborator.
Dolly pushes boundaries as Khloé stays hesitant
Despite Dolly’s matchmaking enthusiasm, Khloé has reportedly remained cautious. She is hesitant to jump back into dating, especially under public scrutiny. Friends claim she appreciated Dolly’s intentions but is unsure whether she’s ready to open her heart again.
Even so, the legendary singer is not backing down. She has started quietly suggesting names and even hinting at setting up casual meet-ups between Khloé and men she believes are “good and honest.”
While the Keeping Up with the Kardashians alum hasn’t committed to anything yet, insiders say Dolly is determined to see her friend happy in love again. Some in their circle believe she might succeed—if Khloé lets her guard down long enough to give someone new a chance.

Jaja has a degree in journalism and took classes in international law and business communication. Her career spans roles at prominent international media outlets, including International Business Times, Celebeat and Delightful Philippines. As a news editor, Jaja covered a wide range of beats, including legal, business, economy, cryptocurrency, personal finance, gaming, technology, and entertainment.