Penelope Cruz and Tom Cruise
After Tom Cruise and Nicole Kidman divorced, Cruise met Penelope Cruz while they were filming the film Vanilla Sky in 2000. They stayed together until 2004, and everyone was sad that Cruise and Cruz were no more. He went on to marry Katie Holmes in 2006 and Cruz married Javier Bardem in 2010.
Ryan Reynolds and Alanis Morissette
Although now we associate Ryan Reynolds with no one but wife Blake Lively, he has had several high profile relationships before. In 2002, he met fellow Canadian Alanis Morissette and the two began dating. They lasted for four years and broke off their engagement in 2006.