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While starring in Heathers, Winona Ryder developed a massive crush on her co-star, Christian Slater. And apparently, their off-screen dynamic was quite the head scratcher. According to the Stranger Things star, she could never tell whether the two of them were dating or not.

But at one point, Slater publicly announced that he and Ryder were getting married. And although he was most likely making a joke, the Beetlejuice star secretly wished he was telling the truth…

Winona Ryder
American actress Winona Ryder at a party for the premiere of the film ‘Night on Earth’ in 1991 in New York City, New York | Catherine McGann/Getty Images

Who has Winona Ryder dated?

Ryder has an impressive dating history with some of the most iconic celebrities in Hollywood. Her first real relationship was with Johnny Depp, and the two of them got engaged after only five months of dating. The Pirates of the Caribbean actor was so sure that Ryder was “the one”, that he got a tattoo that said “Winona Forever” on his bicep.

(It has since been altered to “Wino Forever.”)

Johnny Depp and Winona Ryder
Johnny Depp and Winona Ryder | The LIFE Picture Collection via Getty Images

Following her relationship with Depp, the Beetlejuice star has dated celebs such as Matt Damon, Daniel Day-Lewis, Beck, Chris Noth, David Primer, and Eric Clapton. (Via cinema.com.)

In fact, Ryder has such a badass history of dating musicians that Courtney Love (the lead singer of Hole and Kurt Cobain’s ex-wife) made a joke about her preference for musicians.

According to Rolling Stone, Love blurted to a crowd, “Kurt is gonna leave me for Winona.”

But before all the great romances she’d end up having, Ryder was a sixteen-year-old with a big old crush on her co-star, Christian Slater. Yet unfortunately for the young starlet, she could never figure out whether the two of them were boyfriend and girlfriend or not.

Christian Slater said he was going to marry Winona Ryder

1989: American actors Christian Slater and Winona Ryder pose while holding hands on the red carpet, as they attend the Academy Awards
1989: American actors Christian Slater and Winona Ryder pose while holding hands on the red carpet, as they attend the Academy Awards | Darlene Hammond/Hulton Archive/Getty Images

During an interview with Entertainment Weekly, Ryder confessed that she had “such a big crush” on Slater.

“It’s funny, the last time I watched the movie, I was like, ‘God, we have really great chemistry!’” she said, referring to her on-screen dynamic with Slater. “And I wonder if it was partly to do with the fact that, you know, I wished I could be with him. There were a couple of times where we tried to go out, but there was always some sort of drama…”

But according to Ryder, they had a fling once filming wrapped up. “Nothing happened until after the movie. Then I do remember, like, making out with him a few times.”

“I felt a real closeness to him,” she continued. “Maybe it was because—I’ll just say it—I was a virgin. I remember getting the talk from my mom: ‘When you make out with someone, it doesn’t mean they’re your boyfriend.’ I was like, ‘Really?’ I was always trying to figure out if we were actually dating, and he would never really answer me.”

Christian Slater And Winona Ryder In 'Heathers'
Christian Slater and Winona Ryder standing together in a scene from the film ‘Heathers’, 1988 | New World Pictures/Getty Images

And while on tour, Slater announced that he was going to marry Ryder.

“I remember when we were on the college [publicity] tour, he told the audience we were getting married, which of course sent me into this giggling thing,” said Ryder. “But I remember always thinking, ‘What’s going on? Like, are we…?’ And he never really answered me.”

Are Christian Slater and Winona Ryder friends now?

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Johnny Depp Reportedly ‘Sobbed on Set’ After His Breakup With Winona Ryder

According to Slater and Ryder, they still very much adore one another. Slater told Entertainment Weekly,

“I definitely love her today. She’s a great actress. And that was a unique time for both of us.”

Meanwhile, Ryder gushed about her old co-star during the 2017 Golden Globes.

She said, “I adore him. I love him so much. We started together when I was sixteen years old, and I just always loved him.”