Keanu Reeves & Winona Ryder’s Relationship Through The Years: A Timeline Of Their Bond

Keanu Reeves and Winona Ryder have the sweetest relationship in Hollywood. From ‘Dracula’ – where they may have actually gotten married – to ‘Destination Wedding,’ take a look at how their love bloomed.

Image Credit: AP

It doesn’t take much to get Keanu Reeves to sing the praises of Winona Ryder. “A good friend, sense of humor, intelligence, mind, view of the world, beautiful heart, beautiful spirit and a damn fine actress,” he said to Entertainment Tonight, seemingly unprovoked, during a joint interview with Winona about their 2018 film, Destination Wedding. Ever since the 1990s, these two Hollywood icons have been irrevocably linked, and from listening to them speak about each other, they wouldn’t have it any other way.

What Is Keanu Reeves & Winona Ryder’s Relationship Like?

Seriously, one could hope to find themselves a friendship as warm and loving as the one between Keanu and Winona. “I love Keanu,” Winona Ryder said in a June 2020 interview with The Sunday Times. “We’re great friends. I miss him so much, and it’s hard because he’s not far, just over there,” she said, pointing out a window of her Los Angeles home, indicating that the Bill & Ted star was close enough to be a neighbor. “I’m going to call him now,” she said.

Winona Ryder and Keanu Reeves in 2018 (AP)

“He’s one of my favorite people to work with, to be around,” Winona said in 2018 in a joint-interview with Keanu. The Matrix star added, “I feel the same way about you.”

How They First Met

“We met in the late 80s, like ’87, ’88, at one of the early Independent Spirit Awards at the Hollywood Roosevelt Hotel,” Keanu said in a 2018 interview with PEOPLE magazine. “It wasn’t televised,” added Winona. “Buck Henry was the emcee, and we gave out Best Supporting Actor.” The duo likely awarded Morgan Freeman the inaugural award for his part in Street Smart, since the Independent Spirit Awards didn’t hand out awards for supporting roles until its third incarnation.

From that chance meeting at a burgeoning award show, a deep friendship bloomed. Keanu and Winona began hanging out within a circle of mutual friends. They bonded over “motorcycle rides” and similar interests.

Keanu Reeves and Winona Ryder in A Scanner Darkly (Everett Collection)

Despite their innate chemistry and incredible fondness for each other, Keanu and Winona have never been romantically involved. However, that isn’t to say they haven’t thought about it. When the duo spoke to Entertainment Tonight about why they remember their first encounter so vividly, things got awkwardly adorable. “Well, I had a pretty, pretty big, healthy crush on this guy,” said Winona. “I had a big, healthy crush on you, too,” admitted Keanu. When asked about their healthy crushes, Winona said, “it’s still raging, trust me.”

Past Movies, TV Shows, Projects They’ve Been In Together

It would take four years and a 94-year-old novel for these two to finally share the screen. Reeves and Ryder were first paired up on Francis Ford Coppola’s 1992 film, Bram Stoker’s Dracula. An adaptation of the 1897 novel Dracula, the film saw Keanu cast as Jonathan Harker, the on-screen love of Winona’s Mina Murray. Initially, Coppola didn’t want Reeves for the part. He was hoping to cast Winona’s real-life boyfriend in the role.

“Winona Ryder in those days was going out with Johnny Depp,” Coppola told Premiere magazine in 2005, per Vulture, “and I wanted Johnny to have the part of Jonathan Harker. The studio thought he wasn’t enough of a star. I was so embarrassed.” In 1991, Johnny was a far cry from the star now associated with the blockbuster Pirates of the Caribbean franchise. At the time, Depp was known primarily for his role on TV’s 21 Jump Street, and it would be a few years before his star-making roles in Benn & Joon, What’s Eating Gilbert Grape, and Ed Wood.

In a moment of need, Coppola turned to Ryder for advice. “So, I said to Winona, ‘What do you think? Who do you think they would think is a star who would want to do it?’ And she said Keanu. I just thought he was a very nice person. I was so touched by his sincerity.”

Woody Harrelson, Winona Ryder, Richard Linklater, and Keanu Reeves pose before the premiere of A Scanner Darkly at the Los Angeles Film Festival in Los Angeles, Thursday, June 29, 2006 (AP Images)

Though the critics skewered Keanu’s performance (Screen Rant summed up the complaints, as many called Reeves’ deadpan as being “flat, boring, and abysmal”), there was a definite warmth between Winona and Keanu when they were on-screen.

Keanu and Winona have, as of 2021, appeared opposite each other in three more movies. They reunited in 2006 in Richard Linklater’s adaptation of Philip K. Dick’s sci-fi/drug culture dystopian novel, A Scanner Darkly. Three years later, Reeve and Ryder reunited again on The Private Lives of Pippa Lee, a romantic comedy also featuring Blake Lively, Robin Wright, Alan Arkin, and Julianne Moore. The couple teamed up in 2018 for Destination Wedding. While doing press for that film, Winona would make a startling revelation: she and Keanu had been secretly married for over 25 years.

When Did They Get Married? Are They Still Together?

“We actually got married in Dracula,” Winona told Entertainment Tonight, fulfilling the dreams of every ‘90s kid who wanted these two icons to be an actual item. “No, I swear to god I think we’re married in real life,” she said, before explaining that in the wedding 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.” Keanu, who was also there for that EW interview, didn’t remember things so clearly. “We said yes?” he asked. Don’t you remember that? It was on Valentine’s Day,” she said. “Oh my god, we’re married,” said Keanu.

Keanu Reeves and Winona Ryder in 1992’s Bram Stoker’s Dracula (Everett Collection)

However, without the proper paperwork – or the actual intent – Keanu and Winona’s marriage will only be real in the movies. Still, it has given the close friends something to chuckle about. “Once in a while, I will get a text, ‘Hello, husband,’” Keanu said while speaking with The Talk in 2019. “I didn’t really believe her, and then Francis Ford Coppola, the director of Dracula, contacted Winona and said publicly that, yeah, that really happened, the priest did a full ceremony, and Winona and I got married.”

Actually, neither have been legally married. Winona and Johnny Depp were engaged, but the couple broke up in 1993. She went on to have relationships with Soul Asylum vocalist Dave Pirner and Matt Damon. Since 2011, she’s reported been involved with fashion designer Scott Mackinlay Hahn. The private Keanu has been romantically linked with a few women, and in November 2019, he went public with his romance with Alexandra Grant.

Close Moments They Two Shared Throughout Their History

Things were always so cheerful on Dracula. Winona spoke to The Sunday Times about one scene when she was supposed to act terrified and distraught. Coppola wanted more visible emotion from her and allegedly began hurling insults at her (including “You Whore!”) before calling on her male co-stars to join in. “To put it in context, I’m supposed to be crying,” Ryder said. “Literally, Richard E. Grant, Anthony Hopkins, Keanu … Francis was trying to get all of them to yell things that would make me cry, but Keanu wouldn’t, Anthony wouldn’t. … It just didn’t work. I was, like, really? It kind of did the opposite.”

Winona said she and Coppola are “good now,” but the director denied her version of the events in a statement to PEOPLE. “In this situation, which I remember clearly, I instructed Gary Oldman—in character as Dracula—to whisper improvised words to her and the other characters, making them as horrific and evil as he could. I don’t know what was said, but improvisation is a common filmmaking practice.”

Keanu Reeves and Winona Ryder in 2018’s Destination Wedding (Everett)

Things were a little less tense on the set of The Private Lives of Pippa Lee, but, once again, Keanu came through for his best friend. “Most actors only agree to work on films for a specific amount of time. But I was like, Keep me up there the whole time,” Winona said when discussing the film with BlackBook in 2009. “Little did I know it would be in Danbury, Connecticut, without a rental car, living off of a highway. I had to rely on Keanu, who had the car he drives in the film, to get me to Starbucks.”

Nearly thirty-five years after their first meeting, Keanu and Winona still have that burst of excitement whenever the other one is around. “I meet-cute him all the time,” Winona told Today in 2018 while sitting next to Keanu. “Every time we see each other, it’s a meet-cute.” “I’m meet-cuteing you right now,” added Keanu.

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