March 25, 2023

Keanu Reeves has famously kept his love life under wraps for decades, so the world was largely in the dark about the A-lister’s romantic history. His close friend, actor Josh Richman, told PEOPLE in 2003, “People figure, ‘Keanu Reeves, he should be going out with supermodels.’ But Keanu doesn’t look at it that way. Does he have a girlfriend? I doubt it very seriously. Does he know how to have fun with women? Absolutely. He adores women.”
In 2019, Reeves told Parade that he doesn’t quite understand the world’s fascination with him, but he also doesn’t necessarily mind it, either. “I came to Hollywood to be in movies. I feel really grateful that I’ve had that opportunity, but I’m just a private person, and it’s nice that can still exist,” he said, adding shyly, “Well, I’m not married.”
What a class act! Let’s take a look at Keanu Reeves’ past girlfriends and his relationship with Alexandra Grant. 
No, he’s not currently married, and he never has been … unless you ask Winona Ryder (more on that later).
Reeves and artist Alexandra Grant have been dating since sometime in 2019, and they held hands at a Saint Laurent fashion show that June. They also attended a benefit together a month before that. However, it wasn’t until they walked the red carpet holding hands that November at the LACMA Art + Film Gala that the public finally took notice of the cute coupling.
At the time, PEOPLE reported that the pair had been dating several months. A source dished at the time, “Keanu wants to openly share his life with her. He is extremely happy and grateful to have Alex in his life. [They] started dating earlier this year, but have wanted to keep it quiet.”
Grant joked to Vogue U.K.that the news made her extra popular in her inner circle, but then got serious: “I think every single person I knew called me in the first week of November, and that’s fascinating,” she said. “But the question I’ve been asking in all of this is: ‘What is the opportunity for good?’” When asked if marriage was in the cards, she got understandably cagey (as one might be when you’ve snagged “the Internet’s boyfriend,” after all): “Love at every level is deeply important to my identity. How’s that for dodging the question? I do not believe that isolation is the way. There is a period of isolation that I do as a painter, but I deeply value the experience of being in relationships.”
Reeves and Grant were friends for years before they went public with their romance, and she worked with Reeves. Grant illustrated his 2011 book Ode to Happiness and his 2016 book Shadows. They’re co-owners of X Artists Books, which they co-founded in 2017.
Related: Count Down Keanu Reeves’ 12 Best Roles
It turns out, Ode to Happiness was a sign of how close Grant and Reeves already were. Grant recalled, “The book was made as a surprise, by me, for Keanu, as a private gift. All our friends sitting in the room got the giggles when I gave it to him–they said, ‘Please publish it!’ So that’s how we got into publishing.”
It was rumored that Claire Forlani dated Reeves from 2004 to 2006, but neither of them confirmed any sort of relationship beyond just being friends.
Reeves began dating actress and personal assistant Jennifer Syme after meeting her at a 1998 party for his band, Dogstar. Reeves bought a house, where he lived with Syme, and in 1999 the couple were expecting their first child. Tragically, their daughter, Ava Archer Syme-Reeves, was stillborn on Christmas Eve, about a month before Syme’s due date. Reeves and Syme split shortly afterward. About two years later, Syme died in a car accident after driving drunk.
Reeves has never spoken explicitly about the losses he suffered, but told The Guardian that his experiences with grief in general inspired him in his iconic role of John Wick.
“With any character, the way I think about it is, you have the role on the page, you have the vision of the director and you have your life experience,” he saidadding that his own experiences (which he didn’t specify) were “one of the foundations of the role for John Wick. I love his grief.” He added, “For the character and in life, it’s about the love of the person you’re grieving for, and any time you can keep company with that fire, it is warm. I absolutely relate to that, and I don’t think you ever work through it. Grief and loss, those are things that don’t ever go away. They stay with you.”
Related: Keanu Reeves Talks Screen Violence, Bill & Ted 3 and John Wick: Parabellum
His heartbreaking experience may also have informed his viral moment on The Late Show With Stephen Colbert. When Colbert asked Reeves what he thinks happens when we die, Reeves left Colbert speechless with his response: Taking a deep breath and sighing, Reeves said, “I know that the ones who love us will miss us.”
Reeves and Sandra Bullock never dated, but the Speed co-stars had mutual crushes that neither revealed until years later in separate interviews on The Ellen DeGeneres Show. Check them out gushing and blushing about one another!
In addition to working with Francis Ford Coppola in Bram Stoker’s Dracula, Reeves also dated his daughter! Reeves briefly dated Sofia Coppola in 1992 after working with her iconic father and meeting her on the set.
Reeves and Winona Ryder have been friends for about three decades, and according to Ryder, might actually (maybe) be married…in Romania. She explained to Entertainment Weekly, “We actually got married in Dracula. No, I swear to God, I think we’re married in real life. In that scene, [director] Francis [Ford Coppola] used a real Romanian priest. We shot the master and he did the whole thing. So I think we’re married.”
Reeves also recounted the wedding to The Talk, adding, “Once in a while, I will get a text [from Ryder that says], ‘Hello, husband.'” In 2018, the pair revealed in a joint interview with Vanity Fair that they’ve remained close friends and exchanged handwritten letters and go to dinner together about once a year.
Related: Adam Sandler Wife
Amanda de Cadenet was pregnant with her daughter, Atlanta de Cadenet Taylor, with Duran Duran’s John Taylor when she first met Reeves. “We met when I was two months pregnant, 19 years old, and married to another man,” Amanda wrote in her memoir (via The Daily Mail). “Within minutes of first laying eyes on him, I remember thinking, ‘I wonder how many pregnant women have affairs?’ I was surprised by my strong attraction to a man I had just met.”
Reeves rejected her, but after her divorce from Taylor, she and Reeves went on a single date.
“From the day I got divorced, two years after we first met, I tried every goddamn trick in the book to get him to submit to my advances. Even tried-and-tested seduction tactics, which had otherwise worked with 100 percent success, failed with Mr. Reeves for many years,” she wrote. “He was having none of it, and thank God because had we become lovers at that point, I don’t think we would have the powerful transformative friendship that we have today.”
Actress Jill Schoelen was one of Reeves’ first girlfriends once he hit it big. The pair co-starred in the film Babes in Toyland and were together for about three years.
Next, see inside Jennifer Lopez’s relationships. 
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