4/8

Lester Cohen/WireImage.com

Perhaps her highest-profile relationship, Crow began dating famed (and now disgraced) cyclist Lance Armstrong after meeting at a charity event in October 2003, shortly after he'd divorced his wife and mother of his three children, Kristin Richards. By September 2005, they were engaged and sharing a ranch in Austin. It wasn't meant to be, though, and in February 2006, they'd called split. "After much thought and consideration we have made a very tough decision to split up. We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time," their joint statement read.