Popsugar Celebrity Celebrity Couples Celebrities Who Have Dated Their Costars 18 Actors Who Couldn't Seem to Stop Dating Their Costars June 2, 2018 by Britt Stephens View On One Page Photo 6 of 50 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 6 Gwyneth also dated Brad Pitt, her costar in 1995's Seven. They split in 1997 after three years together. Previous Next Start Slideshow Celebrity CouplesCelebrity FactsCelebrity Breakups