These two Hollywood A-listers have many a famous ex. Winona Ryder might be married to
Keanu Reeves “under the eyes of God,” but her romance with Johnny Depp is what made the 90s.
Matt Damon had a pretty colorful past as well, before meeting his “civilian” wife,
Luciana Barroso . But did you know that Ryder and Damon were once a hot young couple?
It’s even likely that they started dating while he was still in a relationship with Minnie Driver.
Winona Ryder found fame as a teen star in the 1980s and rode her wave of critical acclaim and
big-screen success for a good 30 years now. But there was definitely a time when she was
as well known for her relationship with fellow future A-lister Depp as for her movie roles.
After all, the two were engaged for three years when Winona was in her early 20s.
Johnny even inked himself with a tattoo that declared “Winona Forever,”
which he later edited down to “Wino Forever.” After they split, of course. And while it seems
everyone remembers that romance, most have forgotten that Ryder dated another fellow
future Hollywood star — an up-and-coming actor you might have heard of — Matt Damon.
Legend has it, none other than Ryder’s then-best friend Gwyneth Paltrow introduced
the future lovebirds. It must have happened in December 1997. Whoa, 25 years ago, next year.
We cannot help but mention that Gwyneth was then dating Matt’s best friend, Ben
Affleck. Like, how? Were they coordinating? Matt and Winona hit it off and started
dating shortly after being introduced. However, Gwyneth and Winona, who were pals for a while,
eventually had a falling out. Reportedly after our Miss Paltrow won a best actress
Oscar in 1998 for Shakespeare In Love — supposedly a part Winona was offered first.
Anyway, the early months of Damon and Ryder’s relationship couldn’t have been comfortable.
Though the timeline isn’t concrete, it does seem like Paltrow’s introduction
happened during Damon’s relationship with Good Will Hunting co-star Minnie Driver.
Nearly a decade before Tom Cruise jumped on Oprah’s couch, Damon reportedly told David
Letterman that Driver “pretty much rocked my world.” But when Good Will Hunting opened
nationwide in January 1998, the actor went on The Oprah Winfrey Show to announce that he was single.
Soon after the announcement, he was seen around L.A. with Winona Ryder.
That was a move Minnie found “fantastically inappropriate.” Reportedly, the breakup came
as news to the actor, who then went on a press tour of sorts discussing their sudden separation.
That was a decision that many public figures were weirdly upset by.
“It’s horrendous breaking up with someone anyway, but to have it be so public and to
be cast in a role that I would never play if they were paying me — this wronged woman!” Driver said.
By August 1998, she was no longer taking questions about what happened, though she did share her
frustration regarding the media’s treatment of the situation with The New York Times. Minnie said,
“The press took a spin, chose an angle in the best tradition of Dynasty and Dallas.”
She went on, “The strangest fruit of fame is that people can twist your honesty into what they think
you are trying to project. But how else is one meant to be? Do you become so shut down
that you say nothing, that you have no opinions?” Meanwhile, Damon was enjoying the awards circuit
alongside Ryder. After Good Will Hunting blew up at the box office, Damon and Affleck got
even more good news — the film was nominated for a whopping nine Oscars. In addition,
they guys won for best original screenplay after winning a Golden Globe in the same category.
While Matt brought his mom as his date, Winona was on his arm at the pre-Oscar party in March 1998,
which put the relationship smack in the middle of the spotlight.
From then on, the couple was plagued by media reports of troubles and breakups. However,
nearly two years later, the pair was still together, kissing on the red carpet at the Golden
Globe Awards. Damon was nominated for his work in The Talented Mr. Ripley alongside Gwyneth Paltrow.
Just a month after that Golden Globes appearance, the rumors finally proved to be accurate,
and Matt and Winona had called it quits. After two years together, the Hollywood couple
decided to part ways, and rumors of a romance with Damon’s All the Pretty Horses co-star Penélope
Cruz circulated but were never substantiated. In 2004, Damon was interviewed by Playboy, where
he didn’t shy away from talking about his romance with the Stranger Things star. The actor explained
that he and Ryder had a “great relationship.” Surely, without divulging the actual reason behind
their breakup, Matt said, “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.”
Funny he should say that, because Winona played Richard’s love interest in Autumn in New York,
which was shot in 1999, while she and Matt were still together. Matt Damon,
were you trying to say something here? The guiding force of their breakup was,
perhaps more realistically, Damon’s interest in dating “civilians.” Solely his words.
We’ll touch on that a bit later. For a pairing of two A-listers,
Winona and Matt’s romance slipped by surprisingly under everyone’s radar.
Their commitment to keeping any personal drama out of the press was pretty impressive, especially
considering both parties’ romantic history. Ryder and Damon actually peaked years after
they were a couple. In 2004, Matt shared how he felt concerning the press’s treatment of Winona
following her 2001 shoplifting incident. “When she was being pilloried in the press,
to me, it was like, ‘This too shall pass’ — that somehow her true colors would come out, and she
would get past it because she’s a great woman.” After comparing the blowback to his long-time
buddy Ben Affleck’s romance with JLo, and the whole situation with the media,
he went on, “That part sucks, seeing somebody you care about being treated poorly in public.”
Ryder, too, had kind words for her ex, telling Black Book in 2009,
“Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.” Well,
Minnie probably would disagree, but we’ll have to explore that possibility in our future videos.
Eventually, Matt chose a far-from-famous woman to settle down with. Apparently,
in reaction to the media circus that surrounded Affleck at the time,
Damon said that from then on, he would only date “civilians” — i.e., not celebrities.
Then, what about his flings with Winona Ryder and Minnie Driver? “That was early on,” Damon told the
Sunday Magazine of Sydney, Australia. “These days I definitely only date, as we say, ‘civilians.’”
The actor echoed these sentiments in an interview with the Playboy magazine,
saying, “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.”
True to his word, The Last Duel star brought his civilian girlfriend,
former bartender Luciana Barroso, and her mother with him to promote Bourne Supremacy.
Their small wedding ceremony was held in the Manhattan City Clerk Office in November 2005.
Fifteen years later, they renewed their vows in front of 50 guests. They now share four daughters,
including Barroso’s eldest from a previous relationship, whom Damon considers his own.
The pair celebrated 16 years of marriage last December and remain adorable as ever.
Unlike Matt’s, Winona’s career stalled for a bit after her highly publicized shoplifting arrest
in 2001, but she made a comeback and has stayed on our screens and in our hearts since then. We’ll be
able to marvel at this brilliant actor once again this July, with Ryder coming back as Joyce Byers
in the fourth installment of Stranger things. Concerning her personal life, Winona told OK!
magazine in 2009 that she wants to make sure she’s found Mr. Right before tying the knot.
Well, we don’t know how sure she is that her new beau is Mr. Right, but just about a year later,
Ryder started quietly dating Scott Mackinlay Hahn , the founder of eco-friendly clothing line
Loomstate. They’ve been together for more than a decade now. They are also undeniably adorable.
And though things appear to be going well for the two, it seems unlikely that
they will be tying the knot anytime soon. In 2016, the actor said that she’s pretty
hesitant for Mackinlay to go from boyfriend to husband. “I’m a serial monogamist,” Ryder
shared. “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.
When your parents are madly in love for 45 years, your standards are really high.” Regardless,
she’s been happy with Scott for quite a while now. And despite things not working out between
Winona and Matt, both actors have had nothing but good things to say about
each other in the years following their breakup. A great act to follow, guys!
That’s all we have for you today, Juicers! Which forgotten celebrity couple would
you want us to talk about next? Drop your thoughts in the comments below. As always,
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