Winona Ryder became a go-to actress for movies featuring twisted love stories after starring in Beetlejuice and Heathers in the 1980s. Off camera, Ryder has been looking for The One by staying true to herself.
“I’m a serial monogamist,” Ryder told Net-a-Porter’s The Edit in July 2016. “I was single for a while and dating and … I just didn’t know how to do it!”
The actress explained: “I’ve always been like that. When I was 15, there was a guy I liked, and we made out, and I thought that meant he was my boyfriend. My mom had to explain it to me.”
While Ryder has rarely been single in her life, she has also never made it down the aisle. She did get close after Edward Scissorhands costar Johnny Depp proposed in 1990. The twosome, however, split in 1993 and Depp famously got his “Winona forever” tattoo changed to “Wino forever.”
Winona Ryder Through the Years: From ‘Beetlejuice’ to ‘Stranger Things’
Ryder has since dated several actors and musicians before finding love with Loomstate cofounder Scott Mackinlay Hahn, whom she’s been dating since 2011.
Scroll down to see Ryder’s most high-profile romances over the years:
Lowe was rumored to be dating Ryder in the late 1980s after starring in 1987’s Square Dance. The pair attended the 1988 Golden Globes together, but never confirmed their relationship status.
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Ryder and Slater sparked a relationship after working on 1988’s Heathers, where they played lovestruck teens with a murderous side. “Nothing happened until after the movie,” the actress told Entertainment Weekly in April 2014, reflecting on their origin story. “Then I do remember, like, making out with him a few times.”
Ryder recalled having a “crush” on Slater while filming but claimed they “never went out.” Slater, however, remembered wanting to date her, saying, “we tried” to go out. “I definitely love her today,” Slater told the outlet, noting, “That was a unique time for both of us.”
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One of the most iconic romances of the ‘90s, Depp met Ryder at the New York premiere of Great Balls of Fire! in 1989 and a few months later they went on their first date. The actor proposed to Ryder in July 1990 after five months of dating, despite Ryder being only 17 at the time. That same year they costarred in Edward Scissorhands, playing love interests Edward and Kim.
In June 1993, the pair broke up. “I was very depressed after breaking off my engagement with Johnny 10 years ago,” Ryder told Cinema.com in 2001. “I was embarrassingly dramatic at the time, but you have to remember I was only 19 years old.”
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Ryder moved on with the Soul Asylum singer in 1994 after meeting at an MTV Unplugged session. They parted ways two years later.
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The Little Women actress was briefly linked to Duchovny in 1996. The following year, Duchovny claimed he was “just good friends” with Ryder, telling TV Guide, “I just don’t like to talk about my personal life.”
His former X-Files costar Gillian Anderson had a different story to tell, telling The Guardian in October 2012 that filming in Vancouver was mostly a low-key experience. However, she shared “there were times when paparazzi would come up, if David was dating Winona Ryder, that kind of stuff.”
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Damon met Ryder in 1997 through mutual friend Gwyneth Paltrow, who was dating Damon’s best friend Ben Affleck at the time. Damon and Ryder’s last public appearance was at the 2000 Golden Globes as they broke up later that year.
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The musician was linked to Ryder in 2000, but it wasn’t until 2002 that he commented on the rumored romance. “I met her when I was younger, right before my first record came out,” Beck told Rolling Stone that October. “I hung out with her for a month or two. But talking about any of this is weird unless you’re a complete exhibitionist.”
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The Helmet singer dated the actress for about a year in 2003. Following their split, the band’s 2004 album, Size Matters, featured several songs inspired by Ryder.
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Ryder met Alex-Rubin while working on 1999’s Girl, Interrupted. Ryder didn’t start dating the filmmaker until 2006 and it was a short-lived romance.
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The Stranger Things star dated the Rilo Kiley guitarist from 2007 to 2008. The duo were rumored to be engaged, but they never commented on the speculation.
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Ryder was initially linked to the sustainable fashion company cofounder in 2011 and has since kept most of their relationship private. After four years together, the pair made their red carpet debut while attending New York Film Festival’s premiere for Ryder’s Experimenter in October 2015.
Over the years, the twosome have been spotted on a few red carpets in support of Ryder’s work, but as far as taking their relationship to the next level, the couple isn’t in a rush.
“They may eventually marry but it’s never been a priority, nor has starting a family,” a source exclusively told Us Weekly in June 2022. “[Winona] loves what they have and [they] are perfectly content.”
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