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In 2002, Conor said, "I don't think I would date Winona Ryder. She's kind of old. I like Natalie Portman." Well, the Bright Eyes singer thought wrong. The two had a brief fling that made the indie rocker eat his words.
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Apr 22, 2024 · In 2003, Winona Ryder reportedly had a fling with Conor Oberst. Conor Mullen Oberst (born February 15, 1980) is an American singer-songwriter best known for his work in Bright Eyes. He has also played in several other bands, including Desaparecidos, The Faint (previously named Norman Bailer), Commander Venus, Park Ave., Conor Oberst and the ...
Aug 12, 2022 · A year later, rumors would circulate that Oberst had been dating Winona Ryder, thus living out the dreams of every straight male indie dork in his generational cohort. Lifted was the record that...
- Rob Lowe
- Christian Slater
- Johnny Depp
- David Pirner
- David Duchovny
- Matt Damon
- Beck
- Pete Yorn
- Page Hamilton
- Henry Alex-Rubin
Winona and actor Rob Lowe were linked in the mid-1980s. They went on to star in the 1987 flick Square Dance and later attended the Golden Globes together.
Babies of the ’80s! Winona and Christian Slater were kind of the ultimate “it” couple in their day. The two sparked a romance around 1988 and continued through 1989 when they starred together in the cult classic Heathers. “He broke my heart, or I thought he did at the time,” Winona told Vogue in 1993.
Winona and Christian were an “it” couple, but Winona and Johnny Depp? Simply unmatched. Winona hooked up with her Edward Scissorhands costar in the late ’80s and both fell hard and fast. The couple became engaged in 1990 and Johnny got his infamous “Winona Forever” tattoo at the time. “When I met Johnny, I was pure virgin. He changed that,” Winona ...
Following her breakup from Johnny, the Black Swan actress dated Soul Asylum frontman David Pirner after meeting him at an MTV Unplugged session in 1994. They ultimately called it quits in 1996.
Winona was briefly linked to X-Files star David Duchovny in 1996, after splitting from Pirner. The two only dated for a short moment in time, and we can’t find any pics of them together, but it was definitely the ultimate ’90s pairing!
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. Winona and Matt ended up hitting it off and she accompanied him to the 2000 Golden Globes where he was nominated for The Talented Mr. Ripley, alongside Gwyneth. The couple broke up later that...
Although rocker Beck never officially confirmed their romance, Winona was linked to the musician for a brief time in 2000. When asked about Winona during a Rolling Stone interview a few years after the fact, Beck said, “If you’re seen standing next to somebody, you’re together with them. I’ve been keeping to myself mostly. I met her when I was youn...
Winona loves a rock star! In 2001, the Girl, Interrupted actress was linked to singer-songwriter Pete Yorn.
Winona was linked to another musician, Page Hamilton, Helmet frontman, in 2003. In fact, numerous songs and lyrics on the band’s 2004 album Size Matters were inspired by the actress.
Winona took a brief break from her romances with musicians to date filmmaker Henry Alex-Rubin in 2006. The two initially met while working on Girl, Interrupted and Henry even produced a mokumentary — which she starred in — about Winona’s infamous 2001 shoplifting scandal.
- Cynthia Cook
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Backstory: The pair dated briefly until Winona was arrested for shoplifting in 2001. Quote: N/A Trivia: Another Matt Damon ex, Minnie Driver, also dated Yorn. (Are these pics even Pete Yorn? Why doesn't it look like him to me?) Conor Oberst (35) Period: 2003 Backstory: The two had a fling in 2003. Quote: "I don't think I would date Winona - she ...
Mar 6, 2005 · March 6, 2005. In the indie world, you know you've arrived when you've kissed Winona Ryder. By that criterion, 25-year-old, Omaha-born Conor Oberst, who was snapped snogging Winona two years ago, is already a star.
