On his debut single, Phil Vassar visits his old high school and runs into Carlene, the former "whiz kid in the horn-rimmed glasses" who grew up to be a stunning fashion model. They cruise around in her sports car and he fills her in on his life as an up-and-coming country singer. By the end, they decide to go on a date. Vassar told Songfacts
the song was inspired by Cindy Crawford's rise to fame and an actual girl from his class who had a geek-to-chic transformation.
"The valedictorian of my class was Janice Roque, and I kept thinking about Janice. I'd seen her not long after I got a record deal, and I wrote the song after I was thinking, man, she looked so good. She was this little geeky girl, but she was such a pretty girl, so she's a pretty lady," he explained. "Then I was watching this thing about Cindy Crawford on TV and, of course, it happened that she was valedictorian of her class and she had these little glasses on and I was like, can you imagine she becomes Cindy Crawford, supermodel? So, I thought that was a funny story. Of course, I was a football player and a C student poster child, so it was definitely a stretch that I put us together in the song.
It was really, really fun. I actually got to meet Cindy because of that song. She knew it was about her, and her husband Randy had heard about it and we got to meet. It was really great."