Kenny Chesney recalls his first taste of unrequited love Photo by Charles Sykes/Invision/AP
Kenny Chesney accepts the Pinnacle award at the 50th annual CMA Awards at the Bridgestone Arena on Wednesday, Nov. 2, 2016, in Nashville, Tenn. (Photo by Charles Sykes/Invision/AP)

Believe it or not, Kenny Chesney wasn’t always a hit with the ladies.

I know, we’re thinking the same thing—who would ever reject that adorable, talented, kind and benevolent man?!

Apparently, his college classmate.

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Kenny recently stopped by “Late Night With Seth Meyers” to talk about his Grammy-nominated album, “Cosmic Hallelujah,” and when the topic turned to songwriting, Kenny unleashed a story we’ll never forget.

Kenny didn’t actually write his first song until college, and of course it was for a girl.

“Ironically enough, I was in a persuasion class,” Kenny explained. “There was a girl next to me that I was trying to persuade to go out with me, and I thought I would write her a song. I stayed up at my apartment off campus and I tried to write this girl a song. I put it on a cassette tape … and I took it to class the next day. She sat right beside me in class, and I slid it over to her—didn’t say anything, didn’t even look at her.”

So far, this sounds like a pretty epic plan, but what happens next is, well … not exactly what he had in mind.

“So class ends and I go home [and] come back the next day. Remember, she was sitting right here at this table, and I walked in the next day and she was sitting in the far corner,” he said with a laugh.

Brutal! Can you imagine? I mean, honestly, if a sweet Tennessee boy wanted to write us a song, we’d be thrilled.


But Kenny said it was all good preparation for what lay ahead for him in country music.

“It was literally my first taste of rejection in the music business.”

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And maybe his only taste of rejection, at least in quite a while. Since his debut, Kenny has remained a critical and fan-favorite amongst the country music community, with a career already spanning  more that 20 years and burning hotter than ever before.

We wonder just what that classmate would say now to a song from Kenny?

She’d probably change her tune, that’s for sure!

Samantha Stephens absolutely lives for music. When she's not making it, she's talking or writing about it. She's worked in all arenas of the country music world for nearly a decade, from syndicated radio and television to print journalism. She's even been known to crash a red carpet or two, true story.
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