3. Paris Hilton

Two months after meeting in Palm Springs, Randy Spelling, the brother of Tori Spelling, took Paris Hilton’s virginity. Spelling recounted the story in which he tried to sneak off with the then 15-year-old heiress. The two eventually slipped out to do the deed, but were interrupted by everyone’s worst nightmare. In his own words, Spelling stated: “I hear this knock knock knock on the door, and I look out and her grandma’s there. And then I look out the window and I see Paris in a full-on dress with a suitcase running down the golf course.” Mortified is an understatement.