Since both Aniston and Rudd remained pretty secretive about the romance, the exact timeline of the relationship cannot be explained, but according to some sources, they dated for several years. The pair appeared to be very much into each other in 1998 when they were working on a movie together, the same year Aniston and Brad Pitt began their romance. Rudd and Anniston continued co-starring in Friends from 2002 to 2004.