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.”

Elsewhere in his interview, Chesney shared how his career flourished once he embraced who he really is.

“You know what’s crazy is I had [an] 18-song greatest hits album and nobody knew who I was,” he recalled. “They knew the songs, but I wasn’t comfortable with my skin yet, I didn’t know who I was supposed to be as an artist yet. I would go do shows, and they would go, ‘Oh, yeah, that’s the guy that sings that song,’ and then, ‘That’s the guy that sings that song.’ When I started being my true authentic self, that’s when everything changed.”