Winona Ryder Dating History

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Complete list of Winona Ryder dates, listed in chronological order.

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  •  Profile
  •  Married
  •  Relationship
  •  "Encounter"
  •  On-Screen

Michael Nesmith
Winona Ryder and Michael Nesmith 1986 RUMOR
In the ’80s, a then 15-year-old Winona Ryder was cast in a movie called Square Dance, and since it has the most hillbilly title ever, it was of course produced by none other than Michael Nesmith, which is how the two of them met. During the movie’s filming, Nez grew affectionate towards ... [more]
Charlie Sheen
Winona Ryder and Charlie Sheen 1986
Winona started her career with a bang -- literally. While making her first movie, "Lucas," Winona hooked up with her co-star Charlie. And while these two future tabloid headliners didn't last together, legend has it that it was Charlie who convinced Winona to use a stage name. Thus Winona ... [more]
Rob Lowe
Winona Ryder and Rob Lowe 1986 - 1988
What: Alleged co-star canoodling from 1986-88 It's rumored that while making the 1987 flick "Square Dance," Winona started a fling with Brat Packer Rob Lowe. How that fits in with Rob's other relationships at the time -- with Princess Stephanie and Melissa Gilbert -- is uncertain. [more]
Christian Slater
Christian Slater and Winona Ryder 1988
What: Partners in crime in 1988 Another movie, another on-set romance. While filming "Heathers," things heated up between Winona and co-star Christian Slater, who played a couple on a high school killing spree. Things didn't last between them off-screen, and Winona was devastated. "He ... [more]
Johnny Depp
Johnny Depp and Winona Ryder September 1989 - June 1993
"When I met Johnny, I was pure v*rgin. He changed that. He was my first everything. My first real kiss. My first real boyfriend. My first fiancĂ©. The first guy I had sex with. So he'll always be in my heart. Forever. Kind of funny that word." – Winona. The couple met at the premiere ... [more]
Gary Oldman
Winona Ryder and Gary Oldman 1992 RUMOR
Rumour affair on the sets of "Dracula" in 1992. [more]
Chris Isaak
Winona Ryder and Chris Isaak 1993
Who: Chris Isaak What: Amusement park amore in 1993 Winona and Chris were on a date at Disneyland when they decided to check out the laser light show "Fantasmic." But apparently they found it to be an aphrodisiac, because they started an intense make-out session, according to Scotland's ... [more]
Dave Pirner
Dave Pirner and Winona Ryder 1993 - 1996
"Who: Dave Pirner What: Rock star romance from 1993-96 Dave and Winona met when she attended a taping of "MTV Unplugged" featuring his band, Soul Asylum. The relationship was a total win-win: Winona's Generation X poster girl cred went up, while Dave's burgeoning band got a fame ... [more]
Adam Duritz
Adam Duritz and Winona Ryder 1994 - 1995 RUMOR
What: Requisite canooding rumors in the '90s In the '90s, pretty much every A-list lady hooked up with this Counting Crows frontman, so the rumor was that Winona and Adam had their seven minutes in heaven. (We don't know why this guy gets all the girls, but that's not why we're here.) ... [more]
Dodi Fayed
Dodi Fayed and Winona Ryder 1995 RUMOR
What: Egyptian affection in 1997 Winona and Dodi's alleged hookup is a bit vague. In 1997, Winona vehemently denied that they ever had a fling, telling Us Weekly, "Apparently I am linked to some guy named Dodi something, who I've never even heard of in my life, who's dating Princess Di ... [more]
Daniel Day-Lewis
Winona Ryder and Daniel Day-Lewis 1996 RUMOR
What: Alleged off-screen hookup in the '90s They co-starred in "The Age of Innocence" and "The Crucible," so it didn't take long for rumors of a fling between Daniel and Winona to start flying. Was it because they had an onscreen affair, or was it because they were actually messing ... [more]
David Duchovny
David Duchovny and Winona Ryder 1996
What: Mixed signals in 1997 "I'm happy, and I'm in love." That's how David described his relationship with Winona to TV Guide. But apparently Winona didn't feel the same way. She told columnist Liz Smith she was "completely single" in response. Ouch. No wonder they di ... [more]
David Grohl
Winona Ryder and Dave Grohl 1997 RUMOR
What: Boyfriend stealer in 1997 Winona followed up her stint with Jay by hooking up with Foo Fighters frontman Dave Grohl. The only problem was that Dave was dating Veruca Salt singer Louise Post at the time. So he ditched the rocker for the actress. And although Dave and Winona split after a few months ... [more]
Jay Kay
Winona Ryder and Jay Kay 1997
Jamiroquai singer Jay Kay claimed to have had a fling with Winona Ryder. He said some pretty obnoxious things about her sexual appetite. [more]
Stephan Jenkins
Stephan Jenkins and Winona Ryder 1997
Who: Stephan Jenkins What: The teacher becomes the master in 1997 Just like Charlie Sheen was Winona's first Hollywood romance, Winona was Stephan's. But after she taught him all she could about dating in the spotlight, the training wheels came off, and he rode into the arms of Charlize Theron ... [more]
Matt Damon
Matt Damon and Winona Ryder December 1997 - August 2000
The two were a high-profile couple while together -- 'People' magazine declared them "Hollywood's It Couple" -- despite both their efforts to keep it from the public eye. "There's no advantage to putting it into public consciousness," Damon told GQ in 1999. "It's ... [more]
Jimmy Fallon
Winona Ryder and Jimmy Fallon 2000
Who: Jimmy Fallon What: Funny valentines from 2000-01 Winona tried a new type of man -- the comedian -- when she hooked up with Jimmy Fallon, who was only a few seasons into his run on "Saturday Night Live" at the time. We guess things didn't end too badly, because they looked like they ... [more]
Beck
Beck Hansen and Winona Ryder 2000
What: Short but steamy fling in 2000 What happens when a quirky actress meets a quirky rocker? Fireworks! Beck and Winona made their first public appearance at an Irish music festival, where the singer was performing. Rumour has it that some of the songs on his 2002 album, "Sea Change," were ... [more]
Chris Noth
Winona Ryder and Chris Noth 2000 RUMOR
What: Rebound relationship in 2000 Winona had a "Big" comeback after her split with Matt. She started seeing "Sex and the City" star Chris Noth. It didn't stick so we guess she just wasn't that into him though. [more]
Pete Yorn
Winona Ryder and Pete Yorn 2001
What: Lots of nights (and mornings after) in 2001. This New Jersey rocker had just burst onto the scene with his debut album, "musicforthemorningafter," when Winona broke up with another guy (Jimmy, perhaps?) to date him. But boy, did they have bad timing. Their relationship directly coincided ... [more]
Page Hamilton
Winona Ryder and Page Hamilton 2003 RUMOR
Winona Ryder and Page Hamilton, singer and guitarist in the band Helmet, went out for less than a year. But the two remained friends even after the relationship was over, staying in touch over the phone. [more]
Conor Oberst
Winona Ryder and Conor Oberst April 2003
What: Bright-eyed and bushy-tailed in 2003 In 2002, Conor said, "I don't think I would date Winona Ryder. She's kind of old. I like Natalie Portman." Well, the Bright Eyes singer thought wrong. The two had a brief fling that made the indie rocker eat his words. [more]
Tre Cool
Winona Ryder and Tre Cool 2005 RUMOR
Usually, Winona goes for frontmen and solo artists, so it was kind of surprising when she had a little tryst with Green Day drummer Tre Cool. Naturally, it didn't last. [more]
Val Kilmer
Val Kilmer and Winona Ryder November 2005
Val Kilmer, 46 sure gets around. Winona Ryder, 36 hooked up with Val last November after drinking at Kilmer's rented mansion on Sunset Plaza in West Hollywood. [more]
Henry Alex Rubin
Winona Ryder and Henry Alex Rubin 2006
Henry-Alex Rubin and Winona Ryder met in a somewhat unusual way. Winona starred in his mockumentary about her own shoplifting scandal. They were spotted at a few red carpet events before calling it quits. [more]
Blake Soper
Winona Ryder and Blake Sennett January 2007 - August 2008
"Who: Blake Sennett What: Indie romance from 2007-2008 We were hoping that Blake, who formerly played guitar in Rilo Kiley, would end up being Winona's final fling. There were even (false) rumors that they were engaged. But a month shy of their one-year anniversary, the couple broke up, which ... [more]
Keanu Reeves
Keanu Reeves and Winona Ryder 2008 RUMOR
Tom Green
Winona Ryder and Tom Green August 2008 RUMOR
After Tom Green and Winona Ryder were spotted getting dinner together, rumors swirled that they were a couple. Several anonymous sources claimed that they were hot and heavy, but no proof ever emerged. [more]
James Gooding
Winona Ryder and James Gooding September 2008 RUMOR
Scott Mackinlay Hahn
Winona Ryder and Scott Mackinlay Hahn 2011
Our Winona was there with her boyfriend, Scott Mackinlay Hahn, and wasn’t even that weird about posing with him. He’s an eco-organic (is that a real thing? I just made it up) fashion designer. The line is called Loomstate. Apparently they’ve been together for a couple of years or so ... [more]

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