Really smooth, Kenny… Today, Kenny Chesney is the guest on SiriusXM’s The Howard Stern Show, where he talked about his new memoir “Heart Life Music,” in addition to performing “You and Tequila,” and he also talked about his first ever real rejection that gave him just a taste of what it’s like in the music industry. But he was actually still in college at East Tennessee State University, where he graduated from in 1990… Kenny recalled the first song he ever wrote, which was inspired by a “hot girl” he was sitting next to, ironically, in a persuasion class. He explained that he had been trying to get her attention all semester, and after he ran out of “east Tennessee charm,” he decided to try one more thing: write her a song. It’s actually an incredibly bold move, considering this was well before he had any sort of success as a musician, and like he says, it was his first song: “The first song I ever wrote, I was in college and ironically enough, I was taking a persuasion class, okay? And there was this, this hot girl sitting beside me. I was trying to persuade her all semester to pay attention to me on any level. I was out of jokes and I was out of East Tennessee charm, whatever I had, and so I had nothing. I said, ‘I’m gonna write her a song and see what happens,’ and it was back when you had to push play and record on the recorder. You know, it was one of those things.” But he failed to realize beforehand that the class he gave it to her at was on a Thursday, so he handed over the cassette, then had to wait four days to hear back from her. He got to class and realized the girl was “sitting as far back in the back corner from me as she possibly could”: “I wrote her a song, but I made the mistake of taking it to her on a Thursday, so I came to class, I just slid it over to her. It was on a little cassette, and I slid it over to her, and then I realized that I had to wait Friday, Saturday, Sunday, and Monday, and then go back to that class on a Tuesday to get any kind of response.  All of a sudden, it’s Tuesday and I walk into class and I sat down and I realize that that girl is sitting as far back in the back corner from me as she possibly could.” Ice cold… I refuse to believe it was THAT bad… it actually sounds really sweet. Even if it wasn’t the best song he ever wrote, I think it’s an incredibly thoughtful gesture, though clearly, this girl was not interested… Stern put it this was: “She thought you were a total d***** bag for opening up your heart.” Chesney says that, looking back after 32 years in the music industry, that moment gave him his first taste of real rejection in the music industry, something many artist know about all too well, especially if you get to the point of selling out stadiums like he does now: “Knowing what I know now about the music business and me being in it for 32 years, it was my first taste of real rejection.” We absolutely MUST hear this song now. I’m sure it was pretty rough at the time, but it’s really funny to hear him talk about now, and honestly, I give him major props for being so bold… it certainly paid off in the long run, if he didn’t get this girl. The full video is available below. In 2026, Chesney is headed back to the Sphere for second residency I Go Back 2026, with five shows beginning on Friday, June 19, and wrapping up on Saturday, June 27. View this post on Instagram The post Kenny Chesney Wrote His First Song For A “Hot Girl” In College… & She Sat As Far Away From Him She Possibly Could After Hearing It first appeared on Whiskey Riff.