What All Of Winona Ryder's Exes Have Said About Her

Thanks to her performances in Tim Burton classics "Edward Scissorhands" and "Beetlejuice," the pitch black comedy "Heathers," and the horror classic, "Bram Stoker's Dracula," Winona Ryder positioned herself in the late '80s/early '90s as everyone's favorite alternative pin-up despite being told she would never make it in Hollywood. And several men have done more than just hang posters of the actor on their walls.

Indeed, Ryder might now be happily settled down with Scott Mackinlay Hahn, the fashion designer and co-founder of environmentally friendly and socially conscious brand Loomstate that she first met in 2011. But during her previous two and a bit decades in the spotlight, the two-time Academy Award nominee kept the tabloids busy by dating a string of high-profile guys who no doubt couldn't believe their luck.

So what is it like dating such a pop cultural icon? From alt-rock frontmen to acid jazz singers, not to mention to a whole host of co-stars, here's a look at what 14 exes have had to say about their time with the "Stranger Things" star.

According to some reports, the first of the many celebrities who Winona Ryder dated wasn't Johnny Depp, but another '80s pin-up who later became more renowned for his turbulent private life than his acting talents – Charlie Sheen.

The pair allegedly struck up a connection after appearing alongside each other in the 1986 romantic comedy "Lucas." And although neither party has ever officially confirmed the rumors, Sheen has made a rather bold claim about their time together on set. Yes, in 2012 the "Two and a Half Men" star told CenterStage (via E! News) 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!'" She also disclosed that his one-time co-star has never thanked him for his brainwave, either.

Winona Ryder cemented her cooler-than-cool status in 1989 when she teamed up with Christian Slater to play a pair of murderous lovestruck teens in the brilliant high school comedy "Heathers." And it turns out that the actors' on-screen chemistry spilled over into real life too, without the vengeful killings, obviously.

Speaking to Entertainment Weekly in an oral history of the cult classic, Ryder admitted to getting up, close and personal with her co-star: "Nothing happened until after the movie. Then I do remember, like, making out with him a few times." The star, who played leading lady Veronica Sawyer, also revealed that they tried to take their relationship to the next level but that drama always got in the way.

In the same piece, Slater, who starred as bad boy Jason "J.D." Dean, said that he was so focused on building up a connection with Ryder during filming that he barely acknowledged any of 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.

Indeed, Depp was no doubt left ruing the day he got "Winona Forever" tattooed on his bicep when the pair went their separate ways in 1993 (he later got it changed to "Wino Forever"). According to Mirror, mutual friend Tim Burton later revealed that the heartthrob had confessed who was responsible for the breakup: "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 Los Angeles Times, Depp appeared to blame the pressures of fame for the break-up: "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 testified in favor of her ex-boyfriend in his dramatic libel case involving another former girlfriend, Amber Heard.

You might be surprised to see Keanu Reeves' name in this list. After all, 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!

Yes, while promoting their latest venture together, "Destination Wedding," in 2018, the stars repeatedly claimed that the scene in which their respective characters, Mina Murray and Jonathan Harker, walked down the aisle in during Francis Ford Coppola's horror was undertaken by real priests. For example, in an interview with Esquire (via CNN), Reeves said, "So, I guess we're married under the eyes of God."

Of course, the A-listers' relationship has always been nothing but strictly platonic. However, both parties have confessed to crushing on each other hard back in the day. And in a chat with ET, 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."

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 where the latter was performing.

Like many of the musicians who have dated the "How to Make An American Quilt" star, Pirner allegedly ended up writing a song about Ryder. Taken from 1995's Let Your Dim Light Shine, "Just Like Anyone" is said to be about the actor (sample lyric: "And she starts wonderin' what it's like to be/Liked by everyone and like everyone be just like anyone").

Luckily, their split appears to have been amicable. In 2001, the year that Ryder was 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 (via a fan site), "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. While promoting "Mermaids" in 1990, the actor revealed to Interview 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," the 1989 classic comedy whose fictional high school 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 the former been caught shoplifting in a move that completely derailed her Hollywood career, the latter was asked by SFGate whether his most famous adoring fan had ever stolen anything from him. The singer's curt reply was "My time." Ouch. 

Winona Ryder and Matt Damon spent two years together at the turn of the century, first going public at a pre-Academy Awards bash staged by the now-disgraced movie mogul Harvey Weinstein. Ironically, their last high-profile appearance together also came at an awards bash, the 2000 Golden Globes. But unlike the "Good Will Hunting" star's previous relationship with Minnie Driver, which he famously ended on "Oprah," the split was entirely amicable.

In 2004, Damon told Playboy (via Yahoo! Life), "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." The Oscar winner 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 Damon's split with Ryder did have a monumental impact on his love life, as he explained. "I don't think I could fall in love with a celebrity right now, because it would mean changing my lifestyle," Damon said. "And I like that my lifestyle feels normal to me most of the time." The star stuck to his word when he married Luciana Bozán, an Argentinian who he met while she was working behind a bar, in 2005.

Dave Grohl may be widely regarded as the nicest guy in rock, but that's not a tag that former girlfriend Louise Post is likely to agree with. The Veruca Salt frontwoman was reportedly dumped by the Foo Fighters founder shortly before she was due to go on stage via a phone call. And the reason? Apparently because he'd fallen head over heels for Winona Ryder.

During a 1998 appearance on "The Howard Stern Show" alongside drummer bandmate Taylor Hawkins, Grohl was pressed by a fan about his relationship with the actor. The musician reluctantly confirmed that he did indeed know Ryder adding, "We had met a long time ago," before swerving further questions about whether he'd dated her. When asked if he'd ever seen the "Heathers" star naked, a non-committal Grohl replied, "Well, there's movies and stuff."

In a later interview with Blender (via Foo Archive), Grohl was once again in unconvincing denial mode when the subject of Ryder came up. Apparently putting on the voice of a businessman, the "Times Like These" hitmaker said, "I don't know what you're talking about. I didn't date her. I'm a musician."

Having previously dated Soul Asylum's Dave Pirner, Winona Ryder reportedly began seeing another staple of '90s alternative radio staple at the turn of the century, "Loser" hitmaker Beck. So was there any truth to the rumors?

Well, 17 years later Beck did tell Rolling Stone that he and Ryder weren't exactly strangers: "I met her when I was younger, right before my first record came out. I hung out with her for a month or two. But talking about any of this is weird unless you're a complete exhibitionist."

Unsurprisingly, that's pretty much all the Grammy Award winner has had to say on the subject. In the same interview, he discussed how he wanted his private life to stay private, adding, "I'm not a big believer in the everything's-on-the-table-all-the-time philosophy. I don't understand these people who overexpose themselves. What kind of life is that?" According to some critics, however, Beck did address his relationship with Ryder, albeit in an indirect manner, on his 2003 LP "Sea Change."

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 2000 encounter, 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." And half of the song lyrics suggests that Miller and Ryder had a nice time ("Every other day it's like the day just went/But you make it alright, you make it okay/You make me sorta glad that I waited till today").

However, the other half suggests there's a reason why Miller, who's confirmed live on stage about the origins of the song, and Ryder didn't get to date number two: "How can you have everything and nothing to lose/You and nobody see eye to eye/You're gonna wake up with a ghost instead of a guy." And according to the Dallas Observer, he also once essentially described the "Little Women" star as "cuckoo."

Jay Kay picked up a Grammy, a MTV VMAs Video of the Year, 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 the "Reality Bites" star's grooming habits. And instead of telling the interviewer where to go, the "Virtual Insanity" hitmaker decided to reveal all: "She was very nice and trim down there," he answered (via MailOnline).

If that wasn't disrespecting Ryder enough, Kay also discussed the size of her bosoms before essentially going on to paint her as a sex maniac: "She has these enormous breasts — bigger than they look on film. She did have this habit of wanting to constantly play hide the sausage. It was exhausting." Safe to say, and thankfully so, it was never meant to be for Jamiroquai and Ryder. As well as outing himself as the opposite of a gentleman, the singer exposed himself as a hypocrite. Only two months earlier, he'd chastised former girlfriend Denise Van Outen for spilling details about their relationship to the press.

In 2002, Ryan Adams confirmed all the rumors that he'd dated Winona Ryder when he told the Los Angeles Times that he began seeing the "Girl, Interrupted" star 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, who then explained that he had no problem with living the single life ("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") was still said to have written several songs about his time with Ryder including "Cry on Demand."

However, six years later, Adams either appeared to have forgotten about his dalliance with Ryder or 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 (via NME), "... 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 the "Mr. Deeds" star.

In a 1997 interview with TV Guide, "The X-Files" favorite claimed that he was both happy and loved-up with an unnamed actor reported to be Ryder. The plot thickened when the latter declared at the same time that she was free and single, and then again when Duchovny insisted (via Glamour), "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 possible case for Mulder and Scully. And it was indeed, 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 "The 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."

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 the spell of the "Edward Scissorhands" star, 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 smooth. But in an interview with a fan site several years later, Hamilton revealed that he and the Hollywood star are still in contact.

"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?'" said Hamilton, referring to a gig in which he recalled Ryder's disappointed reaction to his band's 2006 LP, "Monochrome" live on stage. "And I was like, 'What is she talking about?!'" Thankfully, the musician eventually realized what the actor was discussing and was able to put her mind at ease.