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.

Image Credits: Getty Images / Winona Ryder


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!

Image Credits: Archive/WireImage via Getty Images / Kevin Mazur / Winona Ryder and Johnny Depp at the Cry Baby premiere


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.

Image Credits: Getty Images / Barry King / Winona Ryder and Johnny Depp at the Edward Scissorhands premiere


WINONA FOREVER

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. 

Image Credits: Time Life Pictures/DMI/The LIFE Picture Collection via Getty Images / Actors Johnny Depp and Winona Ryder


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. 

Image Credits: Getty Images / Winona Ryder


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.

Image Credits: Getty Images / Johnny Depp


'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. 

Image Credits: Getty Images / Winona Ryder


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.

Image Credits: Getty Images / Jim Smeal / Matt Damon and Winona Ryder at the 1998 Miramax Films Pre-Oscar Party


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.

Image Credits: Ron Galella Collection via Getty Images / Jim Smeal / Winona Ryder and Matt Damon during 57th Annual Golden Globe Awards - Arrivals at Beverly Hilton Hotel in Los Angeles


SWEET PARTING

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.

Image Credits: WireImage via Getty Images / Vera Anderson / Winona Ryder at the "Stranger Things" Press Conference at The London Hotel on June 27, 2019 in West Hollywood, California


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.”

Image Credits: Getty Images / Matt Damon speaks onstage during the "Downsizing" press conference during the 2017 Toronto International Film Festival


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.

Image Credits: Ron Galella Collection via Getty Images / Ron Galella / Actor Rob Lowe and actress Winona Ryder attend the 45th Annual Golden Globe Awards on January 23, 1988 at Beverly Hilton Hotel in Beverly Hills, California


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.

Image Credits: Getty Images / Rob Lowe


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.

Image Credits: Getty Images / New World Pictures / Christian Slater and Winona Ryder for Heathers


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.

Image Credits: Getty Images / Christian Slater


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.

Image Credits: Ron Galella Collection via Getty Images / Ron Galella, Ltd./ Musician Dave Pirner of Soul Asylum and actress Winona Ryder attend "The Age of Innocence" New York City Premiere


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.

Image Credits: Getty Images / Jesse Grant / Beck at the 2018 LACMA Art + Film Gala


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.

Image Credits: Getty Images / Doug Benc / Page Hamilton and Winona Ryder at the Ambassador Hotel benefit, 2003


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!

Image Credits: Getty Images / D Dipasupil / Henry Alex Rubin and Winona Ryder at the Disconnect premiere


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.

Image Credits: Getty Images / Kevin Winter / David Duchovny at the premiere of The X-Files at California Science Center, 2016


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.

Image Credits: Getty Images / Amanda Edwards / Winona Ryder and Keanu Reeves at the photo call for Destination Wedding in Beverly Hills


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.

Image Credits: Getty Images / Keanu Reeves


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.

Image Credits: Getty Images / Kevin Mazur / Winona Ryder and Scott Mackinlay Hahn at the 26th SAG Awards


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.

Image Credits: Getty Images / David Livingston / Winona Ryder and Scott Mackinlay Hahn at the premiere of Stranger Things, 2016


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.

Image Credits: NBCU Photo Bank/NBCUniversal via Getty Images / Kevork Djansezian / Actress Winona Ryder arrives to the 74th Annual Golden Globe Awards held at the Beverly Hilton Hotel


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.”

Image Credits: Getty Images for Coach / Chance Yeh / Winona Ryder attends the Coach 1941 Women's Spring 2017 Show at Pier 76 on September 13, 2016 in New York City


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.

Image Credits: Shutterstock / Winona Ryder


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.

Image Credits: Getty Images / Winona Ryder


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?

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