Keanu Reeves and Alexandra Grant: A Complete Relationship Timeline

MICHAEL TRAN/Getty Images

Keanu Reeves and Alexandra Grant’s Hollywood love story is one for the books…literally.

Though the 59-year-old Matrix actor has reportedly been dating the 50-year-old visual artist since 2019, the pair were friends and colleagues for at least eight years before their relationship turned romantic. In 2011 the pair discovered their professional bond when Grant surprised Reeves with a book called Ode to Happiness, which combined his own writing with her illustrations.

How did this couple go from opening a small press publishing company in 2017 to kissing on the red carpet? Here’s a complete timeline of Keanu Reeves and Alexandra Grant’s relationship with the most recent first.

May 4, 2024: Another art-themed date night in the books for Reeves and Grant! Attending the Hammer Museum Gala in Los Angeles, Grant and Reeves both opted for more casual ’fits than usual. This time Grant paired silky teal pants with a matching leather jacket and white shirt, while Reeves went for a suede suit with a comfortable zip-up underneath. He topped off the look with the same work boots and scarf that he wore to the Museum of Contemporary Art (MOCA) Gala the previous month.

April 14, 2024: Reeves and Grant make their yearly trip to the MOCA Gala, where they shared a sweet kiss in front of the cameras. Grant was dressed in a teal cutout gown with her hair in a braided updo, while Reeves wore a navy suit, gray scarf, and brown suede work boots.

April 1, 2024: According to a source, Reeves and Grant are both “homebodies,” which is why they don't make a bunch of red carpet appearances. "They both work hard and then enjoy life together," the source tells People. “They’re very much a normal couple.”

March 28, 2024: A source tells People that this is “the most fun and positive relationship that Keanu has ever been in.” The source continues, “She is adorable, sweet, caring, and funny. She has her own life and career but is also very supportive of Keanu’s. When he films on location, she travels with him. When he films locally, she often visits the set.”

According to the insider, the pair are officially living together. “Everyone just loves her. They live together and often have friends over for dinner,” the source says. “Keanu is very happy.”

November 4, 2023: Reeves and Grant hold hands at the Los Angeles County Museum of Art’s Art+Film Gala. Both dressed in Gucci; the artist wore a cap-sleeve black gown with a literal keyhole cutout while the actor wore a dapper black suit and bowtie.

September 22, 2023: Grant calls Reeves her “inspiration” at the Los Angeles Beverly Arts Icon Awards. After hitting the red carpet solo, the honoree told People, “The good news about falling in love as an adult is that I had built my own career by the time that my relationship had begun. I feel very confident in the relationship on the red carpet. I feel confident on it alone. It’s interdependent and independent in the best ways.”

Reeves missed the event to perform with his band, according to Grant. “I’m really proud,” she said. “I am a huge Dogstar fan. I had the great pleasure of going to their first public show and because I’ve been listening to the latest album for quite some time, I was one of the only people in the audience who knew all the lyrics. That was really cool. It’s fun. It’s beyond fun.”

Grant also told People about how she and Keanu honor each other’s professional pursuits. “What I love about Keanu and our exchange is that we’re pushing each other to build new roads,” she said. “Seeing the other person’s problem-solving is inspiring, like, ‘Oh, well, okay, this one, that’s a cul-de-sac. How do I try this other thing?’” She continued, “He’s such an inspiration to me. He’s so creative, he’s so kind. He works so hard.”

In fact, Reeves said there has been a notable shift in her work since dating Reeves. “I had a studio visit a few years ago, and this very kind, very high-level person said, ‘I can see that your work has gotten happier,’” she remembered. “That’s real. We’re all human beings. We’re animals. We’re expressing from where we are and certainly feeling happier. I think the work is happier.”

You can read the full interview here.

April 15, 2023: The pair share an uncharacteristic amount of PDA on the Contemporary Art Gala red carpet in Los Angeles.

March 28, 2023: When asked about his “last moment of bliss,” Reeves describes a recent evening with Grant. “A couple of days ago with my honey,” he told People. “We were in bed. We were connected. We were smiling and laughing and giggling. Feeling great. It was just really nice to be together.”

June 4, 2022: The pair attends the MOCA Gala at the Geffen Contemporary in Los Angeles in 2022.

December 21, 2022: Reeves tells Drew Barrymore that in order to be a lover, you have to be a fighter, saying, “If you don’t fight for your love, what kind of love do you have?”

March 11, 2020: Grant opens up about the reactions to her romantic relationship with Reeves. “I think every single person I knew called me in the first week of November, and that’s fascinating,” she told Vogue. “But the question I’ve been asking in all of this is: ‘What is the opportunity for good?’”

When asked if she’s interested in marriage, Grant played coy. “Love at every level is deeply important to my identity,” she said. “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.”

November 5, 2019: A source tells People that Reeves is ready to “openly share his life” with Grant. “He is extremely happy and grateful to have Alex in his life.” According to the source, they officially began dating “earlier this year.”

November 2, 2019: Grant and Reeves are seen holding hands at the 2019 LACMA Art+Film Gala, presented by Gucci.

Though the pair had already attended two events as a couple (that we know of), this was the first time many people on the internet took notice—and reactions were mixed. While some were surprised to see a Hollywood leading man date someone close to their age (at this point, Reeves was 55; Grant, 46), many were thrilled.

June 6, 2019: The pair make their presence known at the Saint Laurent Men’s spring-summer 2020 runway show in Malibu, California.

May 18, 2019: The pair make their red-carpet debut as a couple at a benefit for the Museum of Contemporary Art in Los Angeles.

2017: Grant and Reeves open the X Artists’ Books publishing house.

2016: The colleagues release Shadows, a book of Grant’s photography of her “longtime friend” Reeves.

2011: Grant gifts Reeves “a playful guide to climbing out of depression,” filled with his “poetic texts” and her illustrations.

“The book was made as a surprise, by me, for Keanu, as a private gift,” Grant tells Vogue in 2020. “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.”

This post may be updated.

Originally Appeared on Glamour