Winona Ryder’s Romances: Johnny Depp And The Other Men In Her Life

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


SCOTT MACKINLAY HAHN: HER LONGEST ROMANCE

Ryder’s current 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


SOMEONE'S BEEN SNEAKY

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. To celebrate Earth Day, she was one of the guests attending the show. While we all thought that she was present to take in the clothes, who knew that there was something more going on behind-the-scenes?

Image Credits: Getty Images / Evan Agostini / Winona Ryder at Film Society Gala Tribute to Martin Scorsese


While she had mentioned in passing that she was dating him in 2013, the media didn’t take it too seriously. There were few witnesses who saw the couple at the US Open but that was it. So, 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


MATT DAMON AND THE TALENTED MISS RYDER

Previously, Ryder's been linked with several stars. Starting with the 90s - what does one do, when their boyfriend’s friend is single and they’re looking to double date? Well, Gwyneth Paltrow who's close to Ryder decided to introduce her to her then-current boyfriend, Ben Affleck’s bestie, Matt Damon in 1997.

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


UNDER THE RADAR

For two superstars who were at their peak; and with all of their drama in the spotlight, their getting together actually slipped the public’s notice. Even though it was only for a short while, the couple enjoyed their time together privately, before the media caught onto them at the pre-Oscar party. We barely even have any photographs of them together.

Image Credits: Liaison Agency / Andrew Shawaf / Matt Damon and Winona Ryder in Beverly Hills


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


People didn’t think too much of it as the years passed by. But there was a renewed interest in this couple when Ryder’s team decided to include her time with Lowe in her biography. It’s understood that they might’ve kept their relationship a secret, due to their age difference - Ryder was only 16 while Lowe was actually 23.

Image Credits: Getty Images / Winona Ryder


TOO PRIVATE TO EVEN CONFIRM

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


BEHIND THE SCENES

Ryder also denies this particular pairing. She, in fact, did have a crush on Slater and tried to date him after he broke up with Walker, but it didn’t work out. Slater too, confessed that he always had a crush on Ryder and that he would always be in love with her.


"It’s funny, the last time I watched the movie, I was like, ‘God, we have really great chemistry!’ And I wonder if it was partly to do with the fact that, you know, I wished I could," said Ryder. She remembered there was some sort of drama or the other that made it impossible for them to date.

Image Credits: Getty Images / Kevin Winter / Winona Ryder at the photo call for Destination Wedding


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 Johnny 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


GOING INCOGNITO AND FAILING

But how did she meet the Rockstar? Ryder reportedly wanted to go underground after her very public split with Depp. So, she did what anyone else would do. She decided to move back home - to Minneapolis, hometown to also Dave Pirner. And since she was into indie bands, they were bound to meet.

Image Credits: Getty Images / Winona Ryder at the Paley fest


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.


BECK: THINK I'M IN LOVE?

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. When asked about it, the singer neither confirmed nor denied the relationship. But he was quick to notice the internet’s obsession with Hollywood couples..

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


"If you’re seen standing next to somebody, you’re together with them. I’ve been keeping to myself mostly. I met her when I was younger, right before my first record came out. I hung out with her for a month or two," said Beck. Then in 2001, Ryder was seen with Pete Yorn of Me, Myself, and Irene fame.


A BEAUTIFUL MUSE

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. But Hamilton was very blunt when he was asked what his girlfriend thought about it.


It's understood that if someone writes a song about you, you might think that they're in love with you, and that's exactly what Ryder thought. But the singer dismissed her nonchalantly, hinting that trouble was soon to hit the couple. And not too long after, they ended up parting ways.

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


BLAKE SENNETT: DOES HE LOVE YOU?

She then went on to date Blake Sennett, the guitarist of Rilo Kiley for a year in 2007. Their appearance at the fall 2008 Valentino fashion show in Paris confirmed their relationship. Ryder was actually seen with a band on her ring finger garnering rumours 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!

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


Even though they called it quits pretty soon, the split was amicable. They’ve still stayed friends through the years. Alex-Rubin even invited Ryder as his date to his film’s premiere in 2013. His wife had just given birth to their daughter, 2 days ago and couldn’t make it. Well, isn’t that what friends are for?


ARE THEY OR AREN’T THEY: COMEDIANS, MODELS, ETC.

What could the comedian Tom Green and Winona Ryder have in common? While we are not too sure, this supposed pairing did happen. Reports say that Green actually asked Ryder out after her split with Blake Sennett. And Ryder said yes! They were seen 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. He’d previously dated Australian pop-singer Kylie Minogue, and was seen hiking with Ryder. But nothing became of it. 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


TOGETHER FOREVER

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


Anyone who’s seen them cannot deny the chemistry that the pair have. Even Coppola was excited over their accidental wedding. And while it’s all platonic, the two have worked together on 4 films and have stayed friends. With the pair admitting to having had “big, healthy crush[es]” on each other, we hope they collaborate in the future too.

Image Credits: Shutterstock / Snap / Keanu Reeves and Winona Ryder in Dracula


JOHNNY DEPP: POWER COUPLE OF THE ‘90S

But how can we forget the most influential couple? 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. 

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. The young actress put her all in the relationship, even going to the extent of smoking and drinking, which she never used to partake in previously.

Image Credits: Getty Images / Winona Ryder


WHY DID IT HAVE TO END?

Everyone thought that this couple would last forever. When Depp got the Winona Forever tattoo, its namesake was shocked. "I kept thinking it was going to wash off or something. I couldn’t believe it was real. I mean, it’s a big thing, because it’s so permanent,” recalled Ryder. Depp had replied, “It ain’t goin’ nowhere.”

Image Credits: Getty Images / Ron Galella / Winona Ryder and Johnny Depp at The Silence of the Lambs Century City Premiere


But sadly, the relationship wasn’t permanent. No one really knows why they broke up. But the couple maintain that it was due to the media scrutinizing their every move. Depp told the LA Times,

"It’s very hard to have a personal life in this town. 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."


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, he 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," Ryder shared recently. 

Image Credits: Getty Images / Winona Ryder


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