Winona Ryder & Matt Damon – 2000
Back when Matt Damon and Winona Ryder were in their prime, they were madly in love. They looked happy together whenever they walked the red carpet, and it was indeed a surprise to her about their breakup in 2000 after two years of dating. The former couple never revealed the cause of their split.
Rumors suggested that there was cheating involved from both sides, but nothing ever got confirmed. Damon said he didn’t want to date celebrities anymore, and he got his wish because his wife, Luciana Bozán Barroso, isn’t a public figure. On the other hand, Ruder has been dating Scott Hahn since 2011.
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