After dating multiple A-listers, Winona has kept a solid relationship with someone much more private. Ryder told Rolling ...

Both easy on the eye and regarded as two of the biggest talents of their generation, Matt Damon and Winona ... was dating Ben Affleck, and was also great friends with Ryder. Paltrow introduced ...

Cast your mind back to December 1997 (if you were born!): Gwyneth Paltrow, not yet an Oscar winner nor the queen of GOOP, was dating Ben Affleck, and was also great friends with Ryder. Paltrow ...