Kenny Chesney has maintained a surprising amount of privacy in his personal life given his level of fame. However, he is willing to share some details about his romantic pursuits before he hit the big time.
During a Sunday, October 26, interview with CBS Sunday Morning, the country singer, 57, reflected on writing his first song for a classmate he had a crush on when he was a student at East Tennessee State University.
“She sat right beside me. I tried, I mean, it was six months [trying] to get her to go out with me,” he recalled. “I said, ‘OK, I’m gonna write her a song.’”
He added: “This was the first song that I ever wrote, and it was trying to persuade — and ironically enough, it was in a communications class called Persuasion.”
Chesney recorded the song on a cassette tape and gave it to his crush during a Thursday class. When the two saw each other again the following Tuesday, things didn’t go the way he hoped.
“I came in [like], ‘OK, this is it,’” he said. “She was sitting as far back in the corner of the room as she could sit.”
Despite his disappointment at the time, Chesney credited the experience with teaching him a valuable lesson for his future career.
“That was my first taste of rejection in the music business and as a songwriter,” he explained. “But it went from there, yeah. You listen, you read, you observe people’s lives and you try to communicate that.”
Throughout his decades in the spotlight, Chesney has opted to keep his love life relatively private, but his 2005 marriage to Renée Zellweger made headlines after the pair split four months after their May wedding and finalized their annulment that December.
Of his short-lived relationship with Zellweger, 56, Chesney later claimed on The Oprah Winfrey Show in 2010 that he “panicked” because he “wasn’t ready” for marriage.
Meanwhile, Zellweger addressed speculation about Chesney’s sexuality after she cited “fraud” as the reason for their annulment. Although she clarified at the time of the filing that the term was “simply legal language and not a reflection of Kenny’s character,” rumors still swirled.
“That made me sad,” she told The Advocate in 2016. “It made me sad that somehow people were using that as a way to be cruel and calling someone gay as a pejorative, which has fateful consequences. Of course, there’s the bigger-picture problem of why anyone had to make up a story at all.”
This story was originally reported by Parade on Oct 26, 2025, where it first appeared in the News section. Add Parade as a Preferred Source by clicking here.
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