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Charlie Sheen dated Winona Ryder in the past, but they broke up in 1986. Charlie Sheen is currently available.

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Charlie Sheen

Entertainment - Actor

Why Famous: Charlie Harper of Two and a Half Men

Age: 51 (b. 9/3/1965)

Charlie Sheen Photos (13)

Charlie Sheen's Relationships (23)

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Winona Ryder

Entertainment - Actress

Why Famous: Actress: Girl, Interrupted; Mermaids; Beetlejuice; Heathers; etc.

Age: 44 (b. 10/29/1971)

Winona Ryder Photos (12)

Winona Ryder's Relationships (13)

Relationship Timeline

Event Start Date Length
Dating 1986 --
Broke Up 1986 --

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Relationship Information, Quotes, and Trivia

Where and/or how did Charlie Sheen and Winona Ryder meet?

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Why did Charlie Sheen and Winona Ryder break up?

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