Keanu Reeves' Dating History: Alexandra Grant, Jennifer Syme

There’s no doubt about it, Keanu Reeves is one good-looking guy! The Matrix actor has dated some of the most beautiful women in Hollywood such as Sofia Coppola and his current girlfriend, Alexandra Grant. The pair walked the red carpet together at the LACMA Art and Film Gala and Alexandra has already made a good impression on the actor’s mom, Patricia Taylor.

“What Patricia loves most about Alexandra is her caring nature and the fact that she’s with Keanu for who he is rather than his fame and money,” a source told Closer Weekly in February 2020. Not only that, but Keanu’s mom has “seen a huge change” in her son since he first met Alexandra at a dinner party in 2009.

“He’s more positive about life,” the insider dished. “Seeing her son so happy makes her happy!” But Alexandra is not the only woman who has occupied Keanu’s heart. During a May 2019 appearance on The Ellen DeGeneres Show, Keanu said he used to have a “crush” on his Speed costar Sandra Bullock.

“She’s such a wonderful person, such a wonderful actress,” he gushed. “It was nice to go to work.” Even though Keanu never told Sandra he had feelings for her, the Proposal actress did tell host Ellen DeGeneres that she was smitten with her costar too.

“I think of how sweet Keanu was and how handsome he was,” Sandra gushed about the time they spent together on Speed. “It was hard for me to like, really be serious. Like, he would look at me and I’d be like [giggles]. And I’d have to try to, you know [be serious].”

Despite the undeniable connection, love never blossomed between the two. After they did Speed together, the duo went on to star in the 2006 flick The Lake House where they played a couple who were divided by time.

“I can’t explain in words why Sandra and I have chemistry on-screen or why we work well together. We just do, and I’m glad because I like her tremendously as a person,” the actor previously told Entertainment Weekly, before Sandra chimed in. “I love being around Keanu,” the Blind Side actress marveled. “I really do. He is such a good person.”

Scroll below to see Keanu’s complete dating history!

Winona Ryder

Although Keanu and Winona Ryder were never an item, the Stranger Things actress revealed she and her costar might have mistakenly gotten married when they acted in Bram Stoker’s Dracula.

“In that scene, Francis used a real Romanian priest,” she told Entertainment Weekly in August 2018. “We shot the master and he did the whole thing. So I think we’re married.”

Alexandra Grant

The Constantine actor and Alexandra met at a dinner party more than a decade ago. They went public with their relationship in May 2019. Although the hunk is hush-hush about their romance, he couldn’t be happier to have the visual artist by his side.

Keanu and Alexandra are a “great match” because they “inspire each other on every level,” a source previously told Closer in May 2020. In fact, when the artist’s friends found out she was dating the Point Break actor, they all called her up to talk about her new relationship.

“Every single person I knew called me in the first week of November, and that’s fascinating,” Alexandra gushed to Vogue in March 2020.

It seems like Keanu may have found The One and is looking to take the next step in their relationship.

“Keanu isn’t hiding the fact that he’s going to propose to Alexandra,” a source told Life and Style in April 2022. “His friends know how happy he’s been, he’s talked about making Alexandra his wife and he was recently spotted ring shopping in West Hollywood.”

The insider went on to say that the couple “flow well together” and “mesh perfectly.” They added that the Hollywood heartthrob “adores Alexandra.”