8 “Wait, They Dated?!” Former Celeb Couples
Winona Ryder & Jimmy Fallon
In the context of this slideshow "dated" could very well mean "went on one date and decided to just be friends" which is likely what happened between these two. Still, look at them! I think they make a rather matchy-matchy couple. And the affection between them remains, as Winona gave her first TV interview in six years on Jimmy's show.