Popsugar Celebrity Celebrity Couples Who Has Winona Ryder Dated? Who Has Winona Ryder Dated? See Her Star-Studded Roster of Exes October 29, 2019 by Britt Stephens View On One Page Photo 2 of 14 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 2 Christian Slater Winona and her Heathers costar reportedly struck up a romance between 1988 and 1989, while working on the cult classic. Previous Next Start Slideshow Winona RyderJohnny DeppCelebrity CouplesCelebrity FactsCelebrity Breakups