First, she was in love with Stephen Colletti during her reality show debut on Laguna Beach. When Kristin Cavallari snagged him, she began a relationship with Jason Wahler, which lasted through Laguna Beach (until he cheated on her) and then through the first season of The Hills. Then it was onto Brody Jenner (multiple times), Sean Fox, Gavin Beasley, Stephen Colletti again, Doug Reinheardt, and then Kyle Howard. Lauren Conrad seems to expect the most in relationships, which could be why they have all been so unsuccessful. Unlike the rest of our list, Lauren Conrad is haunted by all of her relationships. Hopefully she meets someone who measures up to her standards.

Image © Paramount Pictures

Story by Nancy Mucciarone

Starpulse contributing writer