Enrique Iglesias Couldn’t Get a Date When He Was a Teenager

When you think of Enrique Iglesias, do the words “shy” and “insecure” come to mind? Probably not. But as it turns out, the smooth crooner we all know and love wasn’t always so, um, smooth, as he revealed on Saturday’s episode of MTV’s When I was 17.

“I wasn’t good with the ladies till I had a hit record,” said the now 35-year-old singer. “I was afraid of being rejected. I just didn’t have the guts to go up to girls and ask them out."

And when he did ask them out, things didn’t always work out. “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. And it was devastating," the singer said. "When you're in high school and a few weeks before prom the girl you’re going with says no, it’s awful, man. At the time, my whole world came crumbling down.” Poor Enrique!

Apparently, he was a sensitive guy back then. “I probably did cry. I hate to admit that now; it's kind of embarrassing. Such a wuss," he confesses. “I went to my prom alone. I know it sounds awful but I went with my friends. We had a good time,” he adds. We’re sure that girl who dumped him in high school is still kicking herself today.