A Glimpse Into Winona Ryder’s Past Romances
As a superstar of the ‘90s with films like Heathers, Winona Ryder is no stranger to the spotlight. Fans and the media have been curious about the Stranger Things actress’ love life, forever! From dating Johnny Depp to marrying Keanu Reeves, she’s been busy. Let’s find out more about all the 'it' couples Ryder has been a part of.
JOHNNY DEPP: POWER COUPLE OF THE ‘90S
Depp and Ryder’s love story was probably that of a modern Romeo and Juliet. They first met at Ziegfeld’s Theater in New York, 1989 and that was it. It was love at first sight. Depp recalls seeing Ryder and everything else fading away like in the movies. How romantic!
Their love blossomed with both of them having similar interests like collecting rare books of Beat poets. They also starred in the cult movie, Tim Burton’s Edward Scissorhands as a couple. Along with Burton, they had been scared that their relationship would hinder the movie but, in fact, their love was its highlight.
Depp was so enchanted by Ryder that he ended up proposing to her just a few months into their relationship. He even got a tattoo which said Winona Forever. They were so head over heels in love and Depp stated that nothing in his life could ever compare to his love for her, confirming just that.
Ryder was equally enamored by him, mentioning that he was her 'first everything'. "He was my first everything. My first real kiss. My first real boyfriend. My first fiancé." the actress said.
A TOUGH BREAKUP
Before Depp, Winona had supposedly only dated Slater for a small period. Depp was her very first and he was devastated when they ended it. According to Tim Burton, a close friend of the couple, Depp too was never the same after their split.
'We were together as a couple for four years, and I counted him as my best friend, and as close to me as family [...] ‘I count our relationship as one of the more significant relationships of my life.’ the actress shared recently.
MATT DAMON AND THE TALENTED MISS RYDER
What does one do when their boyfriend’s best friend is single and they’re looking to double date? Well, Gwyneth Paltrow who was close to Ryder in 1997 decided to introduce her to her then-current boyfriend, Ben Affleck’s bestie, Matt Damon.
Damon was supposedly in a relationship with his Good Will Hunting co-star, Minnie Driver when he first met Ryder. No one knows if he broke up with Driver first or not. But Ryder was there for him when an upset Driver went to the press. Their first appearance at the pre-Oscar party in 1998, confirmed their relationship.
The pair were seen together and in love at the Golden Globes in 2000 but sadly parted ways a year later. When asked about him, Ryder told Black Book that she was lucky to have met him and was on good terms with him.
Damon too spoke about this relationship, but much later. It was 4 years after their break up, that he mentioned Ryder during an interview with Playboy. He supported her when asked about her 2001 incident, saying, “This too shall pass’ — that somehow her true colors would come out and she would get past it because she’s a great woman.”
ROB LOWE AND OTHER FLINGS
Other than the confirmed romances there have been rumors of Winona Ryder dating Rob Lowe. Having starred in Square Dance in 1987 and then attending the Golden Globes the next year together certainly sparked the media’s interest in the couple.
Lowe was in an on-again, off-again relationship with Melissa Gilbert. They were engaged in 1986 but parted ways in 1987. His immediate appearance with Ryder after, was what set off the media buzzing about their relationship. Not only that, the media assumed that they were engaged, but the rumors were squashed with the announcement of the Heathers cast.
CHRISTIAN SLATER: NOT ANOTHER HEATHER
We cannot forget Christian Slater and Ryder’s cult classic, Heathers. Due to their amazing chemistry on-screen as a psychopathic couple, reports flooded in that they had dated during the filming of the movie in 1988. But according to Lisanne Falk who played one of the Heathers in the movie mentioned that Slater was actually dating Kim Walker, the first Heather.
She noticed that the couple were aloof, always hanging out together alone, after the shoot. Falk also mentioned that she was the closest to Ryder and that they would spend time together. Hence, she would have known if Ryder and Slater were a thing, making us question this particular pairing.
DAVE PIRNER’S LOVE SONG
After her intense relationship with Depp, Ryder went through a slew of musicians starting with singer and guitarist, Dave Pirner. The lead of the Grammy-winning Rock band, Soul Asylum seemed to have been a rebound for Ryder after her split with Depp.
She first met him in 1993 during MTV Unplugged. She ended up starring in his band’s music video, Without A Trace, and soon after moved in with him. Their relationship was the most exciting to the public, causing fans to create chaos just to get sight of them. After a couple of years later, they sadly broke up around 1997.
A BEAUTIFUL MUSE
Lo-fi pioneer, Beck who is known for his contribution to Eternal Sunshine of the Spotless Mind’s OST was also supposedly dating Ryder for a short while in 2000. Then in 2001, Ryder was seen with Pete Yorn of Me, Myself, and Irene fame.
Soon in 2003, Ryder dated Page Hamilton of Helmet for a year. What’s so surprising is that most of his songs in his following album, Size Matters is actually inspired by her. She then went on to date Blake Sennett, the guitarist of Rilo Kiley for a year in 2007. Their behavior even garnered rumors that they were engaged.
BACK TO HOLLYWOOD
She then started hanging out with her friend, Oscar-nominated Henry Alex-Rubin who she had met on the sets of Girl, Interrupted. They dated in 2006 with Rubin even getting Ryder to star in a mockumentary about her 2001 incident!
Comedian Tom Green asked Ryder on a date in 2008 making the paparazzi go crazy with dating theories. She also supposedly hung out with James Gooding, a British model, the same year igniting rumors of a romance. While we have no idea how X-Files star, David Duchovny even knows Ryder, they too were linked for a short time in 1996.
DO YOU TAKE KEANU REEVES TO BE YOUR HUSBAND
Everyone was almost certain that something had been going on between Ryder and Keanu Reeves on the set of Dracula. Such was the power of their on-screen chemistry. But sadly, they both denied it, maintaining that they have just been the best of friends. They recently paired up for Destination Wedding, a cute rom-com.
But wait, there’s more! They’re married. Yes, you read that right. Ryder is pretty sure that they accidentally got married while filming Dracula in 1992. The director, Francis Ford Coppola had insisted on using a real priest for their wedding scene with no cuts, who had ended up marrying the two.
SCOTT MACKINLAY HAHN: LOVE OF HER LIFE
Ryder’s longest relationship happens to be with Scott Mackinlay Hahn, who she’s been with since 2011. She’s been very vocal about her love for the fashion designer, choosing to be seen with him at several events. His passion for the environment and the use of organic material for his company is just one of the things that Ryder loves about him.
Surprisingly, we know nothing about Ryder’s longest romance. Both prefer to keep their lives private. Ryder was first seen at Hahn’s launch in 2012. While she had mentioned in passing that she was dating him in 2013, many were shocked to see them together when they made one of their first public appearances at the premiere of Netflix's Stranger Things.
MARRIAGE OFF THE TABLE
Wow, almost 14 famous men in her exciting romantic history! But we are still curious. Why hasn’t she been married despite having such a vivid love life! According to Ryder, she is a “serial monogamist”. She’d rather be in love than be in a failed marriage.
While she jokes about her accidental marriage with Keanu Reeves, even going to the extent of calling him husband, she doesn’t care for it in real life. But she does consider herself a romantic. Citing her parents’ 45 year-long marriage as relationship goals, Ryder told Net-A-Porter,
"When your parents are madly in love for 45 years, your standards are really high. But I’ve been happily with someone for quite a while now.”
AGE IS JUST A NUMBER
With her love life taken care of, Ryder came back into the spotlight after a decade, with Stranger Things. The fact that she lost time or that she got older doesn’t seem to baffle her. She wanted to take a step back from the industry which she had been in since she was a child and just take a breather.
When she came back in the 2010s, she was offered a lot of roles that was motherly. But for once it was liberating to play her own age. While she acknowledges the difficulty of getting good roles due to age, she accepts the importance of each role in a story, whether it's that of a lead or someone’s mother.
Ryder really has led an adventurous life. Being linked with so many handsome men and having close relationships with her co-stars, has certainly run the gossip mill crazy. But the actress has been busy balancing her work life with her personal life. Which couple did you think was going to be the endgame at the time?