Brad Pitt and Jennifer Aniston
1998-2005 Aniston and Pitt began dating in 1998 and married in 2000. The duo remained private about their relationship and appeared to be the perfect couple in public. However, in 2005 the whole of America gasped when Aniston suddenly filed for divorce. Brad rebounded quickly (or maybe he cheated?) with Angelina Jolie and the two became engaged this year. Meanwhile, after many high profile romances that didn't last, Aniston is recently engaged to Justin Theroux.