Once Upon A Prom

MTV Reality TV Show | 2008

In 2008, as part of MTV’s “Once Upon a Prom”, Taylor attended prom at Hillcrest High School in Tuscaloosa, Alabama. “It was literally one of the best nights of my life,” Taylor told People Magazine.

“Platinum record sales. Multiple CMT Music Awards. A Grammy nomination. Eighteen-year-old Taylor Swift has already crossed off some impressive milestones. But as of Friday night, she still hadn’t done one thing: Senior Prom.” — MTV

Taylor attended on the arm of senior Whit Wright, whom she chose from about 50 applicants. “This guy was so down to earth and all-American,” said Taylor, who had been home schooled for the previous two years. “He was unbelievably sweet.”

Taylor picked up Wright in her tour bus. When she discovered that her date was wearing a pink tie and vest to honor a friend’s mother who is battling breast cancer, she ran to the back of the bus and changed into a pale pink dress. “I felt so much like I was in high school again — in a good way, without any drama, without anyone being catty,” said Taylor, who would’ve be on tour when her former high school, Hendersonville High in Tennessee, had its prom. “It was the coolest thing!”

Wright, who bought his date a corsage, told the Tuscaloosa News, “I thought I was going to prom solo and I’m going with Taylor Swift! It’s just been the best senior year I can possibly imagine.”

The pair double-dated with Taylor’s best friend Abigail and his best friend, partying with other seniors on a riverboat known as the “Bama Belle” before heading to the dance.

Watch "Once Upon A Prom"