Reality Love Gone Bad
Lauren Conrad and Jason Wahler, The Hills
The former Laguna Beach star dated Kristin Cavallari's ex on-and-off for a year in 2005. She even visited Jason -- who has had four drinking-related arrests -- in jail once. As a Teen Vogue intern on the MTV series, she also turned down a prestigious summer trip to Paris to spend the summer with him. The two called it quits for good in August 2006.