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Winona Ryder Was Matt Damon’s Last A-List Relationship: Romance Rewind

At the turn of the millennium, Matt Damon and Winona Ryder were one great, and seriously A-list, couple, so let’s look back at their relationship

This seriously A-list couple somehow managed to keep the juicy details of their relationship pretty private, splitting quietly in spring 2000, with Damon denying rumors that he was involved with Penelope Cruz. Both burned by their high-profile previous romances — Damon’s aforementioned awkward breakup from Driver, and Ryder’s notoriously passionate 1989-1993 relationship with Johnny Depp — they clearly had a policy of not talking about each other in public while they were together. While promoting Girl Interrupted around the world throughout 1999, Ryder was tight-lipped about her boyfriend, while Damon would also cagily dodge questions about his love throughout their relationship, usually just praising her acting skills instead.

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