He's known for his legions of female fans and for spending years with leggy tennis phenom Anna Kournikova on his arm. But back in the day, Enrique Iglesias says he was far from a ladies' man.

"I had no luck with the ladies," Iglesias reminisces on the latest episode of "When I Was 17," airing Saturday at 11 a.m. The Latin pop heartthrob, who was 17 in the early '90s, recalls striking out with a lady friend before one of the biggest nights in most teenagers' lives: prom.

"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. It was devastating," the singer reveals. "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."

Iglesias, who has gone on to chart-topping international success with romantic hits like "Hero" and "Escape," concedes that he didn't take the pre-prom dis very well.

"I probably did cry. I hate to admit that now, it's kind of embarrassing," Iglesias says, shaking his head as he mutters, "Such a wuss." Despite the drama, Iglesias ended up heading to the prom without a date and having a blast.

"I went to my prom alone. I know it sounds awful, but I went with my friends. I had a good time," Iglesias said.

Now the "Bailamos" crooner can look back on the experience with a laugh and a message for other teens facing prom night without a dream date.

"For all you guys out there: It's OK to go to prom by yourself," Iglesias assures viewers. "You don't need a date for prom."

"When I Was 17" -- this week featuring Iglesias, Kelly Rowland and Stephanie Pratt -- airs Saturday at 11 a.m. on MTV.