Jennifer Aniston & John Mayer

Poor Jennifer! It's seems like she just can't seem to find the one. After her heartbreaking divorce from Brad Pitt, she rebounded with Vince Vaughn (who is now engaged) and then with Mister Heartbreaker himself, John Mayer. At first it was cute, then it seemed like he was stringing her along. When she took him to the Oscars in February, it seemed like the relationship was finally solid. We were fooled when she allegedly dumped him a month later.