The 35-year-old singer, who is currently dating tennis star Anna Kournikova, admits he was devastated when he was rejected by a fellow student at his high school, MTV reported online.
"I had no luck with the ladies. I was going to prom with this girl that I really liked and she said that she had decided that she wasn't gonna go with me," Enrique said.
"It was devastating. When you're in high school and a few weeks before prom the girl you're going with says no, it’s awful. At the time, my whole world came crumbling down. I probably did cry. I hate to admit that now, it's kind of embarrassing. Such a wuss," he added.
Eventually, the 'Addicted' hitmaker had to go alone to the prom.
"I went to my prom alone. I know it sounds awful, but I went with my friends. I had a good time. For all you guys out there: it's OK to go to prom by yourself. You don't need a date for prom," Enrique said.