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Winona Ryder’s relationship confession: ‘What was I thinking?’

We take a look back at the Stranger Things star's relationship history.
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In the sequel to the iconic film Beetlejuice, Winona Ryder is revisiting a character she last played as a teen. The experience has her thinking about her past, and the relationships that came with it.

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In an interview with Harpers Bazaar published July 11, Ryder explained that parts of her character Lydia Deetz remind her of her younger self.

“In my 30s, I had two disastrous relationships that were—they weren’t wrong, but this was before you would ever think to Google someone,” she said. “When I look back, I’m like, ‘What the hell was I thinking?’ I was dating the type of person who only lets you know a few weeks in that they’re in a relationship with someone else. And you’re just like, ‘What the f**k?’ ”

Although not being specific about who those particular lovers were, Ryder’s dating history includes a host of famous names.

Winona Ryder at Deadline Contenders Television
Winona Ryder (Credit: GETTY)
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Is Winona Ryder married?

While the pair may not have tied the knot, Ryder has been coupled up with her long-time love Scott Mackinlay Hahn, founder of the sustainable organic-cotton company Loomstate, since 2011.

They met at a premiere for Black Swan and he didn’t even recognise her at first. “We connected on so many levels, but it was amazing that he’s not in this business… I really did try to keep it quiet. He thought I was Milla Jovovich. He told me I was great in The Fifth Element,” Ryder told Harper’s Bazaar, adding, “He’s so great. He really is. I’m really lucky.”

While the couple has kept their relationship largely out of the spotlight, sources close to the couple shared with Us Weekly that the pair are simply happy dating, stating, “They may eventually marry, but it’s never been a priority, nor has starting a family. [Winona] loves what they have and they are perfectly content.”

Most recently, the couple have been spotted at film premieres across the globe ahead of Ryder’s return to the upcoming Beetlejuice film.

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Winona Ryder and her partner, Scott Mackinlay
(Credit: Getty)

Who has Winona Ryder dated?

Blake Sennett and Winona Ryder
Blake Sennett and Winona Ryder (Credit: Getty)

Blake Sennett (2007-2008)

From 2007 to 2008, Ryder dated Rilo Kiley guitarist, Blake Sennett.

Rumours of an engagement swirled, but neither has ever confirmed the speculation.

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Henry Alex Rubin and Winona Ryder during 2006 Sundance Film Festival
Henry Alex Rubin and Winona Ryder during the 2006 Sundance Film Festival (Credit: Getty)

Henry Alex-Rubin (2006)

The Stranger Things star dated filmmaker Henry Alex-Rubin in 2006.

The pair met on the set of the 1999 film Girl, Interrupted, but didn’t strike up a romance until much later.

Page Hamilton and Winona Ryder in October 2003.
Page Hamilton and Winona Ryder in October 2003. (Credit: Getty)
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Page Hamilton (2003-2004)

Helmet frontman Page Hamilton dated the actress in 2003 dating for around a year.

Ryder even served as a muse for some of the songs on his band’s 2004 album.

Pete Yorn reportedly dated Ryder in
Pete Yorn (Credit: Getty)

Pete Yorn (2001)

The actress had a short-lived romance with American singer-songwriter Pete Yorn in 2001.

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Beck with a guitar.
Beck was linked to Ryder in 2000. (Credit: Getty)

Beck (2000)

Ryder was linked to rockstar Beck in 2000 and in 2002, the musician shared some insight into that time.

During an October 2022 interview with Rolling Stone, he said,  “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,” he added,

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Matt Damon and Winona Ryder at the Golden Globes.
(Credit: Getty)

Matt Damon (1997-2000)

In 1997, Ryder met Damon through mutual friend Gwyneth Paltrow, who was dating Ben Affleck at the time. Ryder was Damon’s date to the 2000 Golden Globes which was their last public appearance, however, it seems there is no bad blood between the exes.

In a 2009 chat with Blackbook magazine, Ryder shared her love for the Talented Mr Ripley actor, “Matt couldn’t be a greater, nicer guy. I’m really lucky that I’m on good terms with him.”

David Duchovny
(Credit: Getty)
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David Duchovny (1996)

According to Us Weekly, The X-Files actor said he and Ryder were just “good friends” during an interview with TV Guide in 1997, adding that he didn’t like to speak on his personal life.

The pair had been linked in 1996, but his former co-star may have leaked a little more to the story.

Gillian Anderson told The Guardian in 2012, “There were times when paparazzi would come up if David was dating Winona Ryder, that kind of stuff.” Whoops!

Dave Pirner and Winona Ryder
Dave Pirner and Winona Ryder (Credit: Getty)
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David Pirner (1994-1996)

The Heathers star dated the Soul Asylum singer after they met on the set of an MTV Unplugged session in 1994. They split two years later.

Johnny Depp and Winona Ryder arrive at the premiere of Edward Scissorhands
Johnny Depp and Winona Ryder at the premiere of Edward Scissorhands (Credit: Getty)

Johnny Depp (1990-1993)

The Pirates of the Caribbean star was Ryder’s almost husband at age 17. Depp proposed after just five months after starting their relationship and they both starred in Edward Scissorhands together. They never did make it down the aisle though, splitting in 1993.

Depp covered his Winona Forever tattoo to say Wino Forever. While Ryder told Cinema.com in 2001, “I was very depressed after breaking off my engagement with Johnny 10 years ago.”

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“I was embarrassingly dramatic at the time, but you have to remember I was only 19 years old.”

Winona Ryder and Christian Slater
The Heathers co-stars were in a relationship. (Credit: Getty)

Christian Slater (1988-1989)

Ryder and Slater starred together in the 1988 film Heathers but their real-life romance didn’t start until after cameras stopped rolling.

“He broke my heart, or I thought he did at the time,” Ryder told Vogue in 1993.

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Elaborating on how it started she told Entertainment Weekly, “Nothing happened until after the movie,” in an April 2014 chat, “Then I do remember, like, making out with him a few times.”

Rob Lowe and Winona Ryder
Rob Lowe and actress Winona Ryder (Credit: Getty)

Rob Lowe (Late 1980s)

While they never confirmed their relationship status, Lowe and Ryder were linked in the late 1980s. They starred in the film Square Dance together in 1987 and attended the Golden Globes as a pair in 1988.

Beetlejuice Beetlejuice is set to premiere on September 5, 2024.

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