Winona Ryder has been in the spotlight from a very young age, getting her start in blockbusters like Beetlejuice and Heathers and 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 with Johnny Depp to her multiple musician beaus to her current steady partner, Scott Mackinlay Hahn.
Winona and actor Rob Lowe were linked in the mid-1980s. They went on to star in the 1987 flick Square Dance and later attended the Golden Globes together.
Babies of the ’80s! Winona and Christian Slater were 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 classic Heathers.
“He broke my heart, or I thought he did at the time,” Winona told Vogue in 1993.
Winona and Christian were an “it” couple, but Winona and Johnny Depp? Simply unmatched. Winona hooked up with her Edward Scissorhands costar 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.”
Following her breakup from Johnny, the Black Swan actress dated Soul Asylum frontman David Pirner after meeting him at an MTV Unplugged session in 1994. They ultimately called it quits in 1996.
Winona was briefly linked to X-Files star David Duchovny in 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 became Winona’s serious love interest since Depp in late 1997, when they were introduced by Gwyneth Paltrow who 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 for The 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.”
Although rocker Beck never officially confirmed their romance, Winona was linked to the musician for a brief time in 2000.
When asked about Winona during a Rolling Stone interview 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.”
Winona loves a rock star! In 2001, the Girl, Interrupted actress was linked to singer-songwriter Pete Yorn.
Winona was linked to another musician, Page Hamilton, Helmet frontman, in 2003. In fact, numerous songs and lyrics on the band’s 2004 album Size Matters were inspired by the actress.
Winona took a brief break from her romances with musicians to date filmmaker Henry Alex-Rubin in 2006. The two initially met while working on Girl, Interrupted and Henry even produced a mokumentary — which she starred in — about Winona’s infamous 2001 shoplifting scandal.
Back to musicians! Winona dated Rilo Kiley guitarist Blake Sennett from 2007 to 2008. There was talk the two got engaged, although neither party confirmed or denied the rumors.
Word of Winona and MTV comedian Tom Green being 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! The Reality Bites actress has been dating fashion designer Scott Mackinlay Hahn since 2011 and the pair has been seen together at numerous high profile events.
Speaking with The Edit in 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.”
Even though Winona explained why she’s never been married, she may … technically already be married? Back in 2018, the actress revealed to Entertainment Weekly that her onscreen nuptials with Keanu Reeves in 1992’s Bram Stoker’s Dracula had been presided by a “real Romanian priest.”
“We actually got married in Dracula. 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 a video with Esquire 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.