Winona Ryder has been a Hollywood star for over three decades, and her love life has been just as interesting as her movie roles. From rock stars to A-list actors, the “Stranger Things” actress has dated some pretty famous men. What makes her romantic history even more fascinating is that many of these exes have spoken publicly about their time with her. Some comments are sweet, others are a bit salty, and a few are downright surprising. So what did these famous men actually say about dating one of the most beloved actresses of the 1990s?
Christian Slater never got over his crush on her
Most people remember Winona Ryder and Christian Slater as the murderous teen couple in the 1989 cult classic “Heathers.” What many fans don’t know is that their on-screen chemistry turned into a real-life romance after filming wrapped. Ryder was just 16 at the time, while Slater was 19. The relationship was brief, but the impression she left on him clearly lasted. During the movie’s publicity tour, Slater even told an audience they were getting married, which left Ryder confused and giggling about the whole situation.
Years later, Slater has continued to speak highly of his former co-star. In a 2007 interview, he admitted he never got over the crush he had on her during filming. He called her “the woman of my dreams.” When the “Heathers” cast reunited for the film’s 25th anniversary in 2014, Slater said he definitely still loves her today. He praised her as a great actress and called that time a unique period in both their lives. It’s clear this brief romance made a lasting mark on him.
Johnny Depp blamed their fame for the breakup
The relationship between Winona Ryder and Johnny Depp was the stuff of early 1990s tabloid dreams. They met at the premiere of “Great Balls of Fire!” in 1989 and were engaged after just five months of dating. Depp famously got “Winona Forever” tattooed on his arm, a decision that would later need some editing. The couple seemed perfect together, even starring in “Edward Scissorhands.” But by 1993, the engagement was called off, leaving fans everywhere heartbroken and confused about what went wrong.
So why did this famous couple split? According to Depp, the pressure of constant media attention played a huge role. He told the Los Angeles Times that having a personal life in Hollywood was very hard. He felt that being open about their relationship was a mistake because it fed the curiosity instead of satisfying it. Director Tim Burton later revealed that Depp took the blame himself, saying it wasn’t her fault. Despite the breakup, the two remained friends, and Ryder even testified on his behalf during his 2022 defamation case.
Dave Pirner defended her during the shoplifting scandal
After her split from Johnny Depp, Ryder began dating Dave Pirner, the frontman of the rock band Soul Asylum. The two were introduced after the band performed on “MTV Unplugged” in 1993. This relationship was different from her others. Ryder described it as more casual and more like a friendship. She even moved into his home in Minneapolis during their time together. The romance attracted plenty of attention from the press, with one magazine calling Pirner her “boy toy.”
The couple dated until 1996, but Pirner showed loyalty to Ryder years after they broke up. When she was arrested for shoplifting at Saks Fifth Avenue in 2001, many people turned against her. But Pirner stood by his ex-girlfriend. When asked about the scandal, he told reporters that she wasn’t a criminal and that he had nothing but good things to say about her. He also allegedly wrote a song about her called “Just Like Anyone” on Soul Asylum’s 1995 album. The lyrics hint at someone wondering what it’s like to be liked by everyone.
Paul Westerberg gave a surprisingly cold response about her
Winona Ryder was a huge fan of The Replacements frontman Paul Westerberg long before she met him. She even convinced the producers of “Heathers” to name the fictional high school after him. In a 1990 interview, Ryder gushed about the singer, saying she got teary-eyed just thinking about him. She called him her hero and personal god. Given how much she adored him, dating the musician must have felt like a dream come true when they finally got together.
Unfortunately, the feeling didn’t seem to be mutual. When asked in 2002 if Ryder had ever stolen anything from him during their relationship, Westerberg gave a cold reply. He said she stole his time. When the interviewer asked if it was worth more than the items she allegedly took from Saks, he agreed it was. This response came across as bitter, especially considering how much Ryder had publicly praised him over the years. Not every ex has nice things to say, and Westerberg clearly falls into that category.
David Duchovny tried to keep their relationship private
In 1996, rumors started swirling that Winona Ryder was dating “The X-Files” star David Duchovny. However, the actor was extremely private about his personal life and insisted their relationship was just a friendship. When asked about Ryder in 1997, he said they were good friends but that his personal life was an area he didn’t discuss publicly. He kept things mysterious and refused to give any real details about what was going on between them.
But his co-star Gillian Anderson accidentally spilled the beans years later. In a 2012 interview with The Guardian, Anderson mentioned the times paparazzi would show up when Duchovny was dating Winona Ryder. This confirmed what many had suspected all along. Ryder herself has said she feels lucky that most of her relationships happened before the internet and social media took over. She called the intense media attention overwhelming but said it’s nothing compared to what celebrities deal with today. Sometimes keeping things private is the smart choice.
Dave Grohl allegedly left another woman for her
Foo Fighters frontman Dave Grohl reportedly had a short fling with Ryder in 1997, but it came with some drama. According to reports, Grohl ended his relationship with Veruca Salt singer Louise Post to pursue Ryder. Post later claimed Grohl cheated on her with the actress. She even called him out while performing on stage during her band’s Australian tour, saying she was publicly falling apart after finding out about his betrayal.
Grohl has never fully confirmed the romance. During a 1998 appearance on “The Howard Stern Show,” he was asked about his involvement with Ryder. He admitted they had met a long time ago when she was dating Dave Pirner. When asked if he’d seen her naked, Grohl joked there were movies for that. He called her a “classy lady” but refused to openly confirm they dated. Veruca Salt later released a song in 2000 with the lyric about a lover leaving for a movie star, which seemed to be about the whole situation.
Matt Damon said their split was surprisingly normal
Matt Damon and Winona Ryder were introduced by mutual friend Gwyneth Paltrow in 1998. At the time, Damon was riding high on the success of “Good Will Hunting,” and Ryder was the biggest “It Girl” in Hollywood. They quickly became one of the hottest couples in the entertainment world. Their relationship lasted two years before they quietly went their separate ways. Unlike some messy celebrity breakups, this one seemed to end without any public drama.
Damon spoke about the split in a 2004 Playboy interview. He said the relationship ended for reasons far more pedestrian than people might expect. He joked that there was no wild scandal involved. He called Ryder “a great woman” and defended her during her shoplifting troubles, saying he knew her true colors would eventually shine through. Damon later said dating Ryder made him realize he didn’t want to date celebrities anymore. He married Luciana Bozán, a bartender he met in 2003, and they’re still together today.
Keanu Reeves praised her beautiful heart and spirit
Keanu Reeves might seem like an odd name on this list since he and Ryder were never officially a couple. But there’s a fun twist to their story. While filming “Bram Stoker’s Dracula” in 1992, their characters got married in a scene performed by a real Romanian priest. Both actors have jokingly claimed this means they might actually be married in real life. Director Francis Ford Coppola even backed up this theory, saying the wedding scene used a real priest.
Regardless of their legal status, Reeves has always had sweet things to say about Ryder. When asked about her, he listed off her qualities: a good friend, a great sense of humor, an intelligent mind, a unique view of the world, a beautiful heart, a beautiful spirit, and a “damn fine actress.” Both have admitted to having crushes on each other back in the day. Their friendship has lasted for over 30 years, and they’ve continued working together on films like “Destination Wedding” in 2018.
Ryder admitted to making some bad choices in her thirties
While many of Ryder’s exes have spoken about her, she’s also been honest about her own mistakes in love. In a recent magazine interview, the actress admitted that her thirties included two “disastrous relationships” with men who treated her badly. She described dating the type of person who waits a few weeks to mention they’re already in a relationship with someone else. Looking back, she wondered what she was thinking during that time.
Sources close to Ryder have said that men naturally flocked to her, but she wasn’t always good at spotting the bad ones. She probably trusted people without really knowing them first. The actress calls herself a “serial monogamist” who fell hard and fast when she was young. She’s been with fashion designer Scott Mackinlay Hahn since 2011, and friends say they’ve never seen her happier. After years of high-profile romances, it seems she finally found someone who keeps her grounded away from the Hollywood spotlight.
Winona Ryder’s romantic history reads like a who’s who of famous men from the late 1980s through the early 2000s. From co-stars to rock musicians, she’s been linked to some of the biggest names in entertainment. What stands out is that most of her exes still speak fondly of her decades later. Whether it’s Christian Slater saying she’s still the woman of his dreams or Matt Damon calling her a great woman, Ryder clearly left a positive impression on many of the men she dated. Now happily partnered with Scott Mackinlay Hahn, her days of headline-making romances seem to be behind her.
