Every Celebrity Winona Ryder, 53, Has Dated Throughout Her Decades-Long Hollywood Career
Although Ryder might prefer to keep her relationships out of the spotlight, she has made a few rare comments about her lovers
Winona Ryder rarely makes headlines anymore, but back in the 1990s and early 2000s, the Stranger Things actress was on every magazine cover—not for her acting, but for her dating antics. From her short but sweet relationship with Christian Slater to her highly publicized engagement to Johnny Deep, Ryder truly had dated a number of heartthrobs, and we have rounded them all up below!
Rob Lowe
Ryder and Rob Lowe were rumored to be dating after they attended the 1988 Golden Globe Awards together. Now, almost 40 years later, details around their relationship still remain a mystery, and neither party has ever publicly commented on it.
Christian Slater
Ryder met 80’s heartthrob Christian Slater on the set of the 1988 movie Heathers, but according to Ryder, “Nothing happened until after the movie.”
“There were a couple of times where we tried to go out, but there was always some sort of drama,” she continued. “Then I do remember, like, making out with him a few times,”
“I felt a real closeness to him. Maybe it was because — I’ll just say it — I was a virgin. I remember getting the talk from my mom: ‘When you make out with someone, it doesn’t mean they’re your boyfriend.’ I was like, ‘Really?’ I was always trying to figure out if we were actually dating, and he would never really answer me.”
Johnny Deep
Ryder and Johnny Deep were one of the “it” couples of the 1990s. The two met on the set of the 1989 movie Great Balls of Fire! and were engaged five months later. Depp was 27 and Ryder was 18 at the time.
The pair dated up until 1993 and, according to Ryder, that was her “first real breakup, the first heartbreak.”
“I think it was really ironic because everybody else just thought I had everything in the world,” the actress continued. “I had no reason to be depressed; everything was sort of at its peak, but inside I was completely lost.”
Now, in later years, Ryder has opened up even more about their relationship, saying that Depp was “never abusive at all towards me.”
“I only know him as a really good, loving, caring guy who is very, very protective of the people that he loves.”
David Pirner
After parting ways with Depp, Ryder dated singer and songwriter David Pirner, who is best known for being the lead vocalist in the band Soul Asylum. The two met at an MTV Unplugged session in 1994 and remained together for two years. Both of them have been rather tight-lipped about their romantic tryst, though.
David Duchovny
Ryder and X-Files actor David Duchovny were rumored to be together in 1996, but according to him, he “was just good friends with Winona. I just don’t like to talk about my personal life. It’s an area I don’t go into.” Ryder hasn’t commented on this relationship publicly, and it remains unclear if they ever officially dated.
Matt Damon
Ryder met Matt Damon through Ben Affleck, who was dating Ryder and Damon’s mutual friend Gwyneth Paltrow at the time.
Ryder and Damon dated from 1997 until 2000, with Damon saying, “It ended for reasons 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.”
Beck
In 2000, Ryder dated singer and songwriter Beck David Hansen—who is most commonly referred to as “Beck.”
“I met her when I was younger, right before my first record came out,” the singer said. “I hung out with her for a month or two. But talking about any of this is weird unless you’re a complete exhibitionist.”
It is unclear when the pair broke up, but Beck did that interview in 2002, so it’s safe to assume that it was prior to then.
Al Pacino… almost
In 2002, Ryder said that she had a massive crush on her Simone costar Al Pacino; however, he turned her down.
“I was absolutely in love with Al Pacino when I was working with him,” she told Elle earlier this month. “I was actively in love with him. He was obsessed with coffee, and he would take me all over New York–like, to the weirdest places–to try different coffees. I’m 22, or whatever. Finally, he’s dropping me off wherever I’m staying, and I’m like, ‘I love you, you know. I really am completely in love with you.’ And he was like ‘Aw, honey, noooo.”
Page Hamilton
Another singer that Ryder dated was Page Hamilton. They were together from 2003 until 2004, and following the split, Hamilton released several songs with his band The Helmet that were reportedly about Ryder.
Henry Alex-Rubin
Ryder might have met filmmaker Henry Alex-Rubin on the set of Girl, Interrupted in 1999, but the two reportedly didn’t begin dating until 2006. It remains unclear how they began their romance or when it ended, and neither party has ever publicly commented on one another.
Blake Sennett
Rlio Kiley guitarist Blake Sennett dated Ryder from 2007 until 2008 and reportedly even got engaged during that time. Neither Ryder nor Sennett has ever confirmed the rumors ,and they’ve never explained how they met or why they split up.
Scott Mackinlay Hahn
Ryder’s most recent relationship was with fashion designer Scott Mackinlay Hahn. The couple has been together since 2011, and while they don’t comment on their situation often, they do walk the red carpet together from time to time.
Ryder did do a rare interview in 2022 with Harper’s Bazaar, though, where she detailed how they met and how deep their connection really goes.
“He thought I was Milla Jovovich,” Ryder revealed. “He told me I was great in The Fifth Element. We connected on so many levels. But it was amazing that he’s not in this business,” she continued. “I really did try to keep it quiet,”
As of the publication date, Ryder and Hahn are still together.
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