Who: Oscar-nominated and Golden Globe-winning actress Winona Ryder, 47, and Oscar-winning screenplay writer, actor, and producer Matt Damon, 48.

How They Met: Legend has it, Ryder’s then-bestie Gwyneth Paltrow (who was then dating Damon’s bestie, Ben Affleck), introduced the pair in December of 1997. Though the timeline isn’t concrete, this would put Paltrow’s intro during Damon’s relationship with Good Will Hunting co-star Minnie Driver.