Winona Ryderhas been in the spotlight from a very young age, getting her start in blockbusters like BeetlejuiceandHeathersand currently gracing our screens in the hit Netflix series,Stranger Things. Growing up in showbusiness also brings a kinship with other artists and creatives, so it’s no surprise Winona has dating a slew of them!
Below we break down all of Winona’s loves, from her tabloid-fodder relationship withJohnny Deppto her multiple musician beaus to her current steady partner,Scott Mackinlay Hahn.
Rob Lowe
Winona and actorRob Lowewere linked in the mid-1980s. They went on to star in the 1987 flick Square Danceand later attended the Golden Globes together.
Christian Slater
Babies of the ’80s! Winona andChristian Slaterwere kind of the ultimate “it” couple in their day. The two sparked a romance around 1988 and continued through 1989 when they starred together in the cult classicHeathers.
“He broke my heart, or I thought he did at the time,” Winona toldVoguein 1993.
Johnny Depp
Winona and Christian were an “it” couple, but Winona and Johnny Depp? Simply unmatched. Winona hooked up with herEdward Scissorhandscostar in the late ’80s and both fell hard and fast. The couple became engaged in 1990 and Johnny got his infamous “Winona Forever” tattoo at the time.
“When I met Johnny, I was pure virgin. He changed that,” Winona stated in an interview at the time.“He was my first everything. My first real kiss. My first real boyfriend. My first fiancé. The first guy I had sex with. So he’ll always be in my heart.”
After their breakup in 1993, Johnny tweaked the ink to read “Wino Forever” and Winona went on to call their split her “first heartbreak.”
David Pirner
Following her breakup from Johnny, theBlack Swanactress dated Soul Asylum frontmanDavid Pirner after meeting him at an MTV Unplugged session in 1994.They ultimately called it quits in 1996.
David Duchovny
Winona was briefly linked toX-FilesstarDavid Duchovnyin 1996, after splitting from Pirner. The two only dated for a short moment in time, and we can’t find any pics of them together, but it was definitely the ultimate ’90s pairing!
Matt Damon
Matt Damonbecame Winona’s serious love interest since Depp in late 1997, when they were introduced byGwyneth Paltrowwho was dating Ben Affleck at the time. Winona and Matt ended up hitting it off and she accompanied him to the 2000 Golden Globes where he was nominated forThe Talented Mr. Ripley, alongside Gwyneth.
The couple broke up later that year, but Winona has always had good things to say about her ex. “Matt couldn’t be a greater, nicer guy,” she told Blackbook magazine in 2009. “I’m really lucky that I’m on good terms with him.”
Beck
Although rockerBecknever officially confirmed their romance, Winona was linked to the musician for a brief time in 2000.
When asked about Winona during aRolling Stoneinterview a few years after the fact, Beck said,“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.”
He added, “I hung out with her for a month or two. But talking about any of this is weird unless you’re a complete exhibitionist.”
Pete Yorn
Winona loves a rock star! In 2001, theGirl, Interruptedactress was linked to singer-songwriterPete Yorn.
Page Hamilton
Winona was linked to another musician,Page Hamilton, Helmet frontman, in 2003. In fact, numerous songs and lyrics on the band’s 2004 albumSize Matterswere inspired by the actress.
Henry Alex-Rubin
Winona took a brief break from her romances with musicians to date filmmakerHenry Alex-Rubinin 2006. The two initially met while working onGirl, Interruptedand Henry even produced a mokumentary — which she starred in — about Winona’s infamous 2001 shoplifting scandal.
Blake Sennett
Back to musicians! Winona dated Rilo Kiley guitaristBlake Sennettfrom 2007 to 2008. There was talk the two got engaged, although neither party confirmed or denied the rumors.
Tom Green
Word of Winona and MTV comedianTom Greenbeing linked happened around 2008 when the two were spotted going on a date. Nothing was really heard of after that, so perhaps it was a brief dating moment in time.
Scott Mackinlay Hahn
After years of some interesting (and good looking!) men, Winona seems to have settled a bit with a leading man of sorts — and he’s not a musician or actor! TheReality Bitesactress has been dating fashion designerScott Mackinlay Hahnsince 2011 and the pair has been seen together at numerous high profile events.
Speaking withThe Editin a 2016 interview, Winona opened up about why she’s never been married.“I’m a serial monogamist,” she said. “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. But I’ve been happily with someone for quite a while now.”
Keanu Reeves
Even though Winona explained why she’s never been married, she may … technically already be married? Back in 2018, the actress revealed toEntertainment Weeklythat her onscreen nuptials with Keanu Reeves in 1992’sBram Stoker’s Draculahad been presided by a “real Romanian priest.”
“We actually got married inDracula. No, I swear to god I think we’re married in real life,” she said in a joint interview with Keanu at the time. “We shot the master and he did the whole thing. So I think we’re married.”
When Winona reminded Keanu they filmed the wedding scene on Valentine’s Day, Keanu joked, “Oh my gosh, we’re married.”
Keanu then clarified their status in avideo withEsquire on Nov. 22, 2021. While explaining some things about his life and career, he was presented with the question again if he and Winona are “technically” married.
“We did a whole take of a marriage ceremony with real priests,” he quipped. “Winona says we are. Coppola says we are. So I guess we’re married under the eyes of God.”
