Winona Ryder's Exes Have Had Plenty To Say About Her

For over three decades, Winona Ryder has remained a Hollywood staple, and one of the industry's most dynamic actors, capturing the hearts of fans all around the world with her quirky personality, and undeniable talent. With transcendent performances in hits like "Beetlejuice," "Little Women," and "Girl, Interrupted," Ryder became a certified movie star. She has always kept audiences on their toes when it comes to both the roles she chooses, and her eclectic dating history.

The stunning transformation of Winona Ryder has seen the Golden Globe winner change dramatically since first bursting onto the scene, and her romantic relationships have attracted attention from the masses as well. Ryder was in a series of high-profile relationships with famous figures like Johnny Depp, and Matt Damon, and she has been with fashion designer Scott Mackinlay Hahn since 2011. 

Ryder's previous romantic partners seem to hold her in high regard, even decades after their dalliances, and despite never making it down the aisle. (However, according to the actor herself, Winona Ryder and Keanu Reeves were actually married during the filming of "Bram Stoker's Dracula.") Navigating breakups is never easy, and doing it under a media microscope while being a world-famous movie star makes it even harder. Ryder appears to have left quite the impression on her former lovers, as they have all had plenty of things to say about their time with the Hollywood heavy hitter. 

Winona Ryder appeared with Christian Slater in the 1989 cult classic "Heathers." The two portrayed star-crossed lovers who go on a killing spree of their classmates. The actors kept things professional until after the cameras stopped rolling — and then, while their romance was short-lived, Slater became one of Winona Ryder's most famous exes.

Ryder was just 16 at the time of filming, while Slater was 19, and the pair remained close during production before splitting shortly after. "We crossed paths briefly in Sundance, but we don't speak on a regular basis," Slater said of Ryder in a 2007 interview with the Belfast Telegraph. "But I love her. I've never gotten over the crush I had on her then. She is still the woman of my dreams."

Slater continued to sing Ryder's praises in 2014, when the "Heathers" cast reunited with Entertainment Weekly for the film's 25th anniversary. "I definitely love her today. She's a great actress. And that was a unique time for both of us," the "Mr. Robot" alum revealed. He went on to describe how he worked hard to deepen his connection with Ryder for his performance, even ignoring his other co-stars. "I got so into working with Winona that I had blinders on to everyone else. It was almost like J.D. didn't have patience for any of those people, either." 

Winona Ryder's relationship with leading man Johnny Depp made the young couple the talk of the town in the early '90s, and the famous pair even starred together in "Edward Scissorhands" after first meeting at the premiere of "Great Balls of Fire!" in 1989. Ryder and Depp's romance put the duo under a media microscope, and in 1990, Depp proposed to the starlet after dating for just five months.

In a 1991 Rolling Stone interview, Depp gushed about Ryder, and their meaningful relationship. "I'm being really honest with you when I say that there's been nothing ever throughout my twenty-seven years that's comparable to the feeling I have with Winona. ... It's like this weird, bounding atom or something." Despite their powerful connection, and his famous "Winona Forever" tattoo, the couple called off their engagement in 1993. 

The real reason Johnny Depp and Winona Ryder broke up was seemingly their fame. "It's very hard to have a personal life in this town," Depp told the Los Angeles Times in December 1993. "My relationship with Winona, it was my mistake to be as open as we were, but I thought if we were honest, it would destroy that curiosity monster. Instead, it fed it, gave people license to feel they were part of it." The pair remained on good terms following their split ,and in 2022, Ryder even testified on behalf of Depp during his highly–publicized defamation case against his ex-wife Amber Heard.  

Following her split from Johnny Depp, Winona Ryder entered into a relationship with Soul Asylum frontman Dave Pirner. The two were introduced after the band's performance on "MTV Unplugged" in 1993. The Golden Globe winner was allegedly the inspiration behind the band's 1995 song "Just Like Anyone," which featured the lyrics, "And she starts wonderin' what it's like to be/Liked by everyone and like everyone be just like anyone."

Their unexpected romance attracted curiosity, but also scrutiny, from the masses. The musician was referred to as Ryder's "boy toy" by Rolling Stone in a 1994 feature on the movie star. The actor had moved into Pirner's home in Minneapolis during their relationship, and she opened up about their dynamic in the interview, saying, "Our relationship is different than any one I've ever had. It's just more casual. It's more of a friendship, really." Though they broke up in 1996, Pirner remained supportive of Ryder in the ensuing years, particularly in the wake of her shoplifting scandal in 2001.

Ryder was accused of stealing $5,500 worth of designer clothes from a Saks Fifth Avenue store, and was eventually convicted of grand theft. She was placed on three years' probation, and had to pay fines, and complete community service. Pirner defended Ryder when interviewed by the Chicago Sun-Times (via Jae-Ha Kim) in 2002, stating, "She's not a criminal. I've got nothing but good things to say about her."

Winona Ryder reportedly had a brief fling with The Replacements frontman Paul Westerberg, as the actor had a longtime crush on the musician, and even convinced the producers of "Heathers" to name the fictional high school after Westerburg. Ryder was infatuated with the singer, and she raved about him in 1990 to Interview, saying of the punk rocker, "Paul Westerberg is like—I swear, I get teary-eyed when I think about him. If I were to have a hero or a personal god, it would be him."

The couple allegedly had a relationship, but it fizzled out quickly. Despite the actor's adoration of the singer, Westerberg does not seem to share the same sentiment. The only time Westerberg appeared to confirm his romance with the "Stranger Things" star was in a 2002 interview with SFGate, during which her shoplifting incident was brought up. When asked if Ryder stole anything from him when they were seeing one another, Westerberg cooly replied, "My time," before agreeing that it was worth "more than $5,000 at Saks."

For her part, the movie star has remained tight-lipped when it comes to publicly acknowledging many of her past relationships. However, we do know why Winona Ryder never got married. She told Entertainment Tonight, "Marriage? I don't know. I'd rather never have been married than been divorced a few times. Not that there's anything wrong with divorce, but I don't think I could do it if that was a possibility." 

In 1996, rumors spread that Winona Ryder had begun a romance with "The X-Files" star David Duchovny, though the nature of their relationship remains shrouded in mystery. At the time, Duchovny was very private when it came to his personal life, and he insisted things were platonic between the two. "I 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," he said in 1997 via Glamour.

However, his co-star Gillian Anderson seemingly spilled the beans in an interview over a decade after their alleged dalliance. "We weren't in Los Angeles and leaving our houses every day with paparazzi following us. There were times when paparazzi would come up, if David was dating Winona Ryder, that kind of stuff," Anderson revealed to The Guardian in 2012 when discussing her relationship with the paparazzi during production of "The X-Files."

Though Duchovny may have been tight-lipped about his past relationships, Anderson didn't seem to have a problem confirming that he did, in fact, share a romance with the Hollywood superstar. Ryder has since expressed how lucky she was to navigate her fame, and romantic relationships, before the internet took hold of society. "I feel incredibly lucky to have been able to live this life—however intense and overwhelming it got, it's nothing compared to what it is now with the internet and social media," she confessed to Harper's Bazaar.  

Much like her rumored relationship with David Duchovny, Winona Ryder was said to have had a short fling with Foo Fighters frontman Dave Grohl in 1997. Grohl allegedly ended his relationship with Veruca Salt vocalist and guitarist Louise Post in order to pursue a romance with Ryder, though Post later claimed that Grohl was unfaithful to her with the actor. Post famously called out the musician's cheating ways while performing in Australia during the band's 1997 tour.

"I just found out my boyfriend at the time was cheating on me, so I was just publicly falling apart all over Australian stages," Post said to The Music in 2018. The purported relationship between Grohl and Ryder was seemingly referenced in Veruca Salt's 2000 song "Disconnected," which included the revealing lyric, "It's kind of scary when your lover leaves you for a movie star." 

During a 1998 interview on "The Howard Stern Show," Grohl appeared with his Foo Fighters bandmate, Taylor Hawkins, and he was questioned about his involvement with Ryder by a fan. "We had met a long time ago when she had been going out with Dave Pirner from Soul Asylum," Grohl said while remaining mum about just how deep their relationship ran. The musician later called Ryder "a classy lady" while on the show but refused to openly confirm any romance between the two, and Ryder herself has never publicly commented on the nature of their rumored fling. 

Oscar winner Matt Damon is undeniably one of Ryder's most recognizable exes. The actors were introduced to one another by a mutual friend, Gwyneth Paltrow, in 1998. The pair quickly became one of Hollywood's hottest couples, as Ryder was the "It Girl" of the silver screen, and Damon was riding high on the success of "Good Will Hunting." The couple dated for two years before they amicably split, and Ryder became the last celebrity Damon openly dated.

"I don't think I could fall in love with a celebrity right now, because it would mean changing my lifestyle, and I like that my lifestyle feels normal to me most of the time," Damon told Playboy via Fortune City when reflecting on his previous high-profile relationships, before later calling Ryder "a great woman." Damon also touched on the reason behind their split, 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," he joked, referencing her film, "Autumn in New York."

Ryder and Damon appear to share a mutual respect for one another, even many years after their split, as the actor also had positive things to say about her ex. "Matt couldn't be a greater, nicer guy. I'm really lucky that I'm on good terms with him," she said to Black Book via Us Magazine. 

Winona Ryder apparently had a fondness for musicians, as she reportedly had a short fling with indie singer-songwriter Beck in 2000, following her split from Matt Damon. Their relationship didn't last long, and Beck didn't even publicly comment on their romantic dalliance until 2002, in an interview with Rolling Stone. "I met her when I was younger, right before my first record came out. I hung out with her for a month or two. But talking about any of this is weird unless you're a complete exhibitionist," he bluntly told the publication.

The Grammy winner has not openly acknowledged his relationship with Ryder since, and as is the case with most of her past partnerships, neither has the actor. Since her brief romance with Beck over two decades ago, she has apparently gone on to find true love. Winona Ryder and Scott Mackinlay Hahn, a fashion designer, have been together since 2011, after the pair met at the 2010 premiere of "Black Swan." Hahn has been supportive of Ryder's career, and has accompanied her to various awards shows, and red carpet events.

Shortly after dating Ryder, Beck married actor Marissa Ribisi in 2004, and they had two children together before ultimately divorcing in 2021. As with his alleged romance with Ryder, Beck has largely stayed silent about his separation from Ribisi, though he did describe his divorce as "heartbreaking" to The New Yorker. 

Winona Ryder and Old '97s' lead singer Rhett Miller allegedly went on just one date in 2000, though the sole interaction seemed to provide creative fuel for the musician. Lyrics in the band's 2001 song "Rollerskate Skinny" seemingly address his one and only date with Ryder, and Miller also confirmed on stage that the tune is about the "Edward Scissorhands" star. 

"It was a really weird time in my life because I was kind of all of a sudden getting pursued by a Hollywood star, which is pretty rare," Miller said while performing at a Nashville venue (via Good Lord Lori on YouTube). "For years I never said anything about it because it was kind of a funny little time, but now she's mentioned it enough to the press where I feel like I don't give a s***." Miller went on to confirm the celebrity in question was Ryder while preparing to sing the song on stage, calling her "very cool and nice." In the same video clip, Miller also claimed that Ryder called "Rollerskate Skinny" her favorite song ever written about her.

The name "Rollerskate Skinny" is a nod to J.D. Salinger's literary classic, "The Catcher in the Rye." In it, Holden Caulfield's sister, Phoebe, is described using the quirky terminology by the main character. Ryder has referred to the acclaimed novel as her "bible," and has claimed to have read it nearly 50 times (via Hazlitt Magazine). 

In 2003, Winona Ryder started a relationship with Helmet frontman Page Hamilton, and the band's 2004 album "Size Matters" features songs, and lyrics, inspired by his time spent with the A-list actor. Tracks like "Everybody Loves You," and "Throwing Punches," are just a few tunes that nod to Ryder, hinting that their romance might have been plagued by drama. 

However, it also appears that things ended amicably, as Hamilton referenced the actor in a 2007 interview with Mark Prindle. "My ex-girlfriend was on the cover of Vogue magazine – I just had dinner with her parents, she's a doll," Hamilton revealed in the sit-down, proving that the former couple were still on good terms three years after their breakup. "The article said her last relationship was with a non-famous musician from Oregon and New York, and her parents were so embarrassed. I said, 'My friends tease me about it, I thought that was awesome.'" 

The musician didn't seem upset by the media's depiction of him during, or after, his romance with Ryder. "It's just so great. I love that I've been able to continue doing what I love doing without being invaded by that side of it," he said, referencing the pitfalls that come with fame. Ryder had previously been a fan of Helmet, and has praised the album inspired by her. Hamilton revealed in the same interview that she prefers "Size Matters" to their album that followed, "Monochrome."