The strawberry blonde surprised everyone when she started dating DJ Samantha Ronson. After 16 months of a dramatic, public romance, the couple called it quits. While Lindsay claimed they were taking a break so she could focus on her career, Sam said she simply couldn't take the paparazzi anymore. "To be honest, being with her was more of a headache than anything else," Ronson told The Times magazine. Jeff Vespa/WireImage.com - February 5, 2009
Lindsay Lohan's Journey to Jail
Take a look back at the troubled star's ups and downs, from "The Parent Trap" to the pokey.