40 Celebrity Couples You Forgot Dated In The Early ’00s
Matt Damon and Winona Ryder
Matt Damon and Winona Ryder were introduced in the late ’90s by Gwyneth Paltrow. Gwyn was really close friends with Winona at the time and was dating Ben Affleck, Matt’s Boston BFF. Matt and Winona actually fell apart around the same time that Ben and Gwyn did, but we’ll get to that in a second. Matt and Winona went to the Golden Globes together in 2000 Matt was nominated for an award for The Talented Mr. Riply with Gwyn — talk about a power friend group. Neither couple lasted long after the show, but Winona has said since that Matt is an awesome dude and they’re on good terms.