They say you should never kiss and tell — but apparently nobody told
that to Winona Ryder's exes. So what do we know about the star's past relationships?
According to some reports, Charlie Sheen was the first of many celebrities to date Winona
Ryder. The pair allegedly struck up a connection after appearing alongside each other in the 1986
rom com Lucas. And although neither party has ever officially confirmed the rumors,
Sheen has made a rather bold claim about their time together on set. In 2012, the Two and a Half
Men star told CenterStage that he was responsible for coining Ryder's stage name. Sheen recalled:
"We were listening to The Doors, to 'Riders on the Storm.' [Winona's] real name is Horowitz.
And I said, 'You know, I'm thinking Winona Ryder sounds cool,' and she was like, 'Yeah!'"
Sheen also claimed that his one-time co-star never thanked him for his apparent brainwave, either.
In 1989, Winona Ryder cemented her cooler-than-cool status when she
teamed up with Christian Slater to play a pair of murderous lovestruck teens in the brilliant
high school comedy Heathers. It turns out that the actors' on-screen chemistry spilled over into real
life too — albeit without the killing. Speaking to Entertainment Weekly for an oral history of
the cult classic, Ryder admitted to getting up close and personal with her co-star. She said:
"Nothing happened until after the movie. Then I do remember, like, making out with him a few times."
"You got power… power I didn't think you had."
Ryder also revealed that they tried to take their relationship to the next level. Sadly,
drama always seemed to get in the way.
In the same piece, Slater said that he was so
focused on building a connection with Ryder during filming that he barely
acknowledged his other co-stars. And he still holds a fondness for her, adding:
"I definitely love her today. She's a
great actress. And that was a unique time for both of us."
Winona Ryder's most famous relationship was undoubtedly the four years she spent with
her Edward Scissorhands co-star Johnny Depp. The pair first met at the premiere of Great
Balls of Fire! in 1989 and a year later they announced their engagement. Sadly,
love's young dream failed to make it down the aisle.
"Goodbye."
Depp was no doubt left rueing the day he got "Winona Forever" tattooed on his bicep when
the pair went their separate ways in 1993. Their mutual friend, Tim Burton, later revealed that the
heartthrob had confessed who was responsible for the split. He told The Los Angeles Times:
"I felt so bad. I asked him why it happened but all he said was,
'It wasn't her fault, it was mine.'"
But in an interview with the same outlet,
Depp appeared to blame the pressures of fame for the break-up. He said:
"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."
The pair still remained friends, however, and in 2022 Ryder publicly defended her ex during
his ongoing libel case against his ex-girlfriend, Amber Heard.
One of Winona Ryder's most serious celebrity relationships was with Dave Pirner,
the frontman of "Runaway Train" alt-rockers Soul Asylum. The pair dated between 1994 and
1996 after reportedly meeting at an MTV Unplugged taping at which Pirner was performing. Like many
of the musicians who have dated Ryder, Pirner apparently ended up writing a song about her;
in this case, it was "Just Like Anyone," a track from 1995's Let Your Dim Light Shine.
Pirner and Ryder's eventual split appears to have been amicable. In 2001,
the year that Ryder was famously arrested and charged with shoplifting, Pirner was asked by
The Chicago Sun-Times whether his ex-girlfriend should walk free or be sent to jail. He replied:
"She's not a criminal. I've got nothing but good things to say about her."
It seems fair to say that Winona Ryder once idolized Paul Westerberg,
frontman of punk icons The Replacements. In 1990, the actor revealed to Interview
Magazine that she was brought to tears whenever she thinks of the musician, adding:
"If I were to have a hero or a personal god, it would be him."
You can find further evidence of Ryder's fandom in Heathers, which takes place in
a fictional high school that she insisted be named in honor of Westerberg. So the
actor no doubt had to pinch herself when she began dating the man of her dreams.
Unfortunately, Ryder didn't appear to make the same kind of impression on Westerberg. In 2002,
just a year after Ryder was caught shoplifting, Westerberg was asked by SFGate whether his
most famous adoring fan had ever stolen anything from him. The singer simply said:
"My time."
Winona Ryder and Matt Damon spent two years together as a couple,
first going public at a pre-Academy Awards bash staged by the now-disgraced movie
mogul Harvey Weinstein. But unlike Damon's previous relationship with Minnie Driver,
which he famously ended on Oprah, their split was entirely amicable. In 2004, Damon told Playboy:
"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."
"Ooh, he's sexy!"
Damon also defended Ryder in the wake of her shoplifting scandal, adding:
"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."
But the actor's split with Ryder did have a monumental impact on his love life. He explained:
"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."
Damon stuck to his word when, in 2005, he married Luciana Barroso,
an Argentinian woman who he met while she was working behind a bar.
Winona Ryder only went out on one date with Rhett Miller, the frontman of "loud folk"
outfit Old 97's. But she must have made quite the impression during their encounter in 2000,
as the musician later dedicated an entire song to the night in question.
Named after the way in which Phoebe Caulfield is described by
her brother Holden in J.D. Salinger's classic novel The Catcher in the Rye,
"Rollerskate Skinny" appears on the band's 2001 fifth studio effort, Satellite Rides.
Half of the song's lyrics suggest that Miller and Ryder had a nice time on their date,
but the other half suggests there's a reason why they didn't get to date number two. The song asks
why Ryder can "have everything and nothing to lose," points out that "you and nobody see eye
to eye," and suggests that she's "gonna wake up with a ghost instead of a guy." Less artfully,
in an interview with the Dallas Observer, he once indirectly described her as "cuckoo."
In 2002, Ryan Adams confirmed the rumors that he had dated Winona
Ryder when he told the Los Angeles Times that he began seeing her after breaking
up with a previous long-term girlfriend. However,
they both realized that the time wasn't right and went their separate ways soon after. Adams added:
"I'm sometimes bad around people because I just don't have a lot to
say. I'm inward. I love to people watch [...] on a plane, in a restaurant."
Adams went on to explain that he had no problem with living the single life, although he is still
said to have written several songs about his time with Ryder, including "Cry on Demand."
Six years later, however, Adams either appeared to have forgotten about his dalliance with Ryder
— or, at least, he might have attempted to rewrite his romantic history. In a blog post titled "Facts
About Me," the singer-songwriter insisted that he and the actor were only ever platonic, adding:
"But she is my friend and I will always love her."
Is there something about being with Winona Ryder that makes men lose their memories? Alongside Ryan
Adams, David Duchovny also appears to be confused about the nature of his relationship with her.
"I was hoping you could help me solve the mystery of the horny beast."
In a 1997 interview with TV Guide, the X-Files star claimed that he was both happy and loved-up
with an unnamed actor, who was reported to have been Ryder. The plot thickened when the latter
declared at the same time that she was free and single, and then again when Duchovny insisted:
"I was just good friends with Winona. I just
don't like to talk about my personal life. It's an area I don't go into."
It all sounds like a case for Mulder and Scully. Indeed, it was Duchovny's co-star Gillian Anderson
who seemed to solve the mystery for everyone in a 2012 interview with The Guardian. Referring to the
level of press intrusion the pair suffered at the height of X-Files mania, she said:
"We weren't in Los Angeles and leaving our houses every day with paparazzi following us. There were
times when paparazzi would come up, if David was dating Winona Ryder, that kind of stuff."
Case solved, it seems.
Jay Kay picked up a Grammy, an MTV VMAs Video of the Year award,
and even a Guinness World Record back in his heyday as frontman of acid-jazz
favorites Jamiroquai. And judging by the crude interview he gave to FHM about his
brief fling with Winona Ryder, he should also have been crowned Least Chivalrous Pop Star.
In 2005, Kay was asked by the men's magazine about Ryder's grooming habits. And instead
of telling the interviewer where to go, Kay decided to reveal a number
of incredibly intimate details about his ex. If that wasn't disrespectful enough,
Kay also discussed the size of her breasts before essentially going on to paint
her as a sex maniac. As well as outing himself as the opposite of a gentleman,
the singer exposed himself as a total hypocrite: Only two months earlier, he had chastised former
girlfriend Denise Van Outen for spilling details about their relationship to the press.
Winona Ryder added to her list of rock star lovers in 2003 when she briefly dated Page Hamilton,
the frontman of alternative metal outfit Helmet. And like most musicians who have
fallen under Ryder's spell, the singer-guitarist ended up writing songs about their time together.
In fact, much of 2004's Size Matters is said to be about Ryder. The fact that the album contains
tracks titled "Enemies," "See You Dead" and "Throwing Punches" would suggest that their
relationship didn't exactly run smoothly. But in an interview with a fan site several years later,
Hamilton revealed that he and the Hollywood star are still in contact. Referring to a past gig
at which he had recalled Ryder's reaction to his band's 2006 LP Monochrome, Hamilton said:
"I got a text from my ex-girlfriend last night that said something to the effect of,
'I heard you talked about me at the Melvins' show,
do you still love me?' And I was like, 'What is she talking about?!'"
Thankfully, the musician eventually realized what
Ryder meant — and was apparently able to put her mind at ease.
You might be surprised to see Keanu Reeves' turn up here, since he and Winona Ryder have
never really been linked as a romantic couple. But if you believe the pair's story about their
time filming Bram Stoker's Dracula in 1992, then the pair were once technically married!
"No!"
Yes, while promoting the movie Destination Wedding in 2018, both stars repeatedly
claimed that the Dracula scene in which their characters walk down the aisle was
undertaken by real priests. For example, in an interview with Esquire Reeves said:
"So, I guess we're married under the eyes of God."
Of course, the A-listers' relationship has never been anything but strictly platonic. That said,
both parties have confessed to crushing on each other hard back in the day. And in a
chat with Entertainment Tonight, Reeves reeled off a list of qualities he admired in Ryder:
"Good friend. Sense of humor. Intelligent mind. View of the
world. Beautiful heart. Beautiful spirit. And a damn fine actress."