Cindy Crawford

Even before Cindy Crawford became one of the most sought-after supermodels across the globe, she was dating her high school sweetheart, Bill Cordes. They were even crowned as Prom King and Queen back then. However, their young love changed when Cindy was discovered by a talent scout and started gaining attention in the fashion industry. Sadly, the two said their goodbyes as she pursued a career in modeling.

Over the years, Cindy dated many A-listers in Hollywood and even married some of them like Pretty Woman actor Richard Gere. She was also linked to John F. Kennedy, Jr. and Val Kilmer, before settling with former model Rande Gerber. They have two children who followed in their parents’ footsteps and are now models themselves. With the couple’s earnings and proper investment planning, their children are probably set for life.