36. Jay Cutler and Kristin Cavallari
You might recognize Kristin Cavallari from the popular reality show “The Hills” or MTV’s reality “Laguna Beach: The Real Orange County,” but did you know she was dating the Chicago Bears quarterback Jay Cutler? Perhaps, if you’re a big fan of the show. What you probably didn’t know is that the two almost never got a chance to meet. It was the NFL star who courted after the reality star, and the first time he asked her out, she turned him down.
How does one turn down an NFL superstar, you ask? At the time, Cavallari didn’t even know Cutler was an NFL player. She was busy shooting “The Hills,” and so moving to Chicago wasn’t an option for the aspiring actress. It was another year before Cavallari traveled to Chicago with her mother and remembered Cutler’s offer. This time, she attended a Bears game, later calling up Cutler and accepting his invitation, only 12-months after he’d made it. Fortunately for her, Cutler was still single, and his ego didn’t stand in his way of getting the girl.