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  1. May 31, 2022 · One of the more forgotten couples in Hollywood is the former pairing of Matt Damon and Winona Ryder, whose relationship began under semi-controversial circumstances.

  2. Dec 17, 2023 · Matt Damon and Winona Ryder dated for over two years, and he later explained why he decided not to date anyone else famous after they split.

  3. Jul 4, 2019 · 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...

  4. Nov 28, 2020 · Matt Damon and Winona Ryder have been linked to several famous people over the years. But did you know they once dated each other? That’s right! The pair dated back in the late ’90s/early...

  5. May 26, 2022 · Matt Damon became Winona’s serious love interest since Depp in late 1997, when they were introduced by Gwyneth Paltrow who was dating Ben Affleck at the time.

  6. Dec 14, 2023 · Though she didn't name the new girlfriend — and Damon and Affleck both took their mothers as their official plus-ones to the Oscars that year — Damon and Winona Ryder had been photographed...

  7. Oct 28, 2011 · Matt, now 41, chose a far from famous woman to settle down with when he married bartender Luciana Barroso in 2005. The couple has three daughters together in addition to Luciana's...