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Pete Yorn (41)Period: 2001Backstory: The pair dated briefly until Winona was arrested for shoplifting in 2001. Quote: "Our relationship is different than any one I've ever had. David Duchovny (55)Period: 1996Backstory: There's nothing to it, it was a fling, although they insist they were just friends. Quote: On the Howard Stern show, Grohl called Winona "a classy lady."Trivia: Their relationship is referenced in the Veruca Salt song Disconnected: "It's kind of scary when your lover leaves you for a movie star."Matt Damon (45)Period: 1997-2000Backstory: The pair were introduced by Ryder's now-former friend Gwyneth Paltrow, who at the time was Damon's BFF's Ben Affleck's girlfriend. They dated for three years and the breakup was, in Matt's words, "far more pedestrian than, say, a mad orgy at the Four Seasons during which my feelings were hurt because Richard Gere was too interested in her." So no drama, it just ended. I'm really lucky that I'm on good terms with him."Trivia: Since their relationship was hounded by rumors of cheating on both sides, Matt was quick to deny reports he was dating co-star Penelope Cruz soon after he and Winona broke up.Since then, Ryder has kept a relatively low profile and appeared in only a handful of films.In 2006, she had a leading role in , the animated adaptation of a Philip K. The futuristic story explores the impact of Substance D, a mysterious, addictive drug, on its main characters.

“The thing she especially can’t stand is how all of Johnny’s middle-aged friends, even Tim Burton, are cheering this relationship on like it’s appropriate, when Winona is telling her own friends that it’s absolutely not. “I’d rather never have been married than been divorced a few times.But I’ve been happily with someone for quite a while now.”WATCH: Winona Ryder on Abuse Allegations Against Ex Johnny Depp – ‘It’s Upsetting For Me to Wrap My Head Around’" data-reactid="31"WATCH: Winona Ryder on Abuse Allegations Against Ex Johnny Depp – ‘It’s Upsetting For Me to Wrap My Head Around’Ryder is currently dating fashion designer Scott Mackinlay Hahn, whom she’s reportedly been in a relationship with since 2011., after taking a lengthy break from Hollywood.Winona Ryder's dating history is the stuff of legend. Chapter One: Tom Cruise Chapter Two: Brad Pitt Christian Slater (46)Period: 1988Backstory: The two kids dated briefly while filming the iconic cult classic Heathers. It didn't end well, probably due to miscommunication over how exclusive they actually were. Quote: "I don't think I would date Winona - she's kinda old.A reporter for Sassy once asked some alternative rockers if they would go out with her, explaining, "It's my theory that boys start bands so they can get famous enough to attract Winona Ryder." Courtney Love once said, "You're no one in music until you have feuded with me or until you sleep with Winona." In short, Winona had her share of fun. Quote: “We went out for two weeks and he broke my heart, or I thought he did at the time.” (Slater maintains he has no idea what she's talking about)Trivia: Slater continues to think highly of Winona, telling a journalist a couple of years ago he doesn't understand the "she's crazy" party line and that he still loved her. I like Natalie Portman."Trivia: Oberst maintains they were just friends. Jamiroquai/Jay Kay (45)Period: 2003Backstory: The musician from that video that tripped everyone out in the 90s had a fling with Winona and no one would've known about it had he not brought it up years later in a gross, dickhead way.

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