After splitting from actress Claire Forlani in 2006, Keanu Reeves has been romantically linked to artist Alexandra Grant since 2019

Keanu Reeves is notoriously private about his love life — and understandably so.

When Reeves stepped onto the red carpet on Nov. 2, 2019, for the LACMA Art + Film Gala in Los Angeles with his rumored girlfriend, artist Alexandra Grant, it sent fans into a tizzy. But the outing wasn’t particularly shocking to Grant’s friend, actress Jennifer Tilly, who told Page Six in February 2020 that the couple had been dating for much longer than fans realized.

“I remember a couple of years ago, about a year and a half ago, [Grant] said, ‘Keanu Reeves is my boyfriend,’ and I’m like, ‘Wait. What? What? What?'” Tilly told the publication.

She continued, “It’s really astonishing to me how in the last five months, all of a sudden, she goes to an event with him and everybody goes insane, like, ‘It’s his new girlfriend,'” before adding, that Grant “had gone to a lot of events with him [in the past].”

It’s just suddenly surfaced that he’s been dating her for several years,” Tilly added.

The John Wick actor hasn’t spoken publicly about his relationship with Grant or the A-list stars he’s previously dated. However, in December 2021, Reeves offered his perspective on love on The Drew Barrymore Show after host Drew Barrymore said she was “not a fighter” but rather a “lover.”

Reeves replied, “No, no, because if you’re a lover, you gotta be a fighter. … Because if you don’t fight for your love, what kind of love do you have.”

He then got out of his seat and laughed, joking that Barrymore got him “philosophical” about love.

Here’s a look back at Keanu Reeves’ dating history.

Jill Schoelen

COURTESY EVERETT COLLECTION

The pair met when they were filming one of Reeves’ first films, Babes in Toyland (1986), and were rumored to have dated for almost three years.

Directly after their split in 1989, Schoelen began dating another rising star, Brad Pitt, after she met him on the set of Cutting Class.

Sofia Coppola

RON GALELLA

COLLECTION VIA GETTY

Reeves dated the then-up-and-coming director after meeting her on the set of Bram Stoker’s Dracula, directed by Sofia’s father, Francis Ford Coppola. The pair reportedly dated briefly before splitting up in 1992.

Winona Ryder

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The former costars never dated, but they may be technically married! Ryder told Entertainment Weekly that, while on the set of the 1992 film Bram Stoker’s Dracula, the pair may have accidentally been wed for real by a Romanian priest.

Ryder explained, “In that scene, Francis [Ford Coppola] used a real Romanian priest. We shot the master, and he did the whole thing. So I think we’re married.”

The pair laughed about the revelation in the interview, which they did while promoting their 2018 rom-com Destination Wedding.

Amanda de Cadenet

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Reeves was linked to the ’90s personality, but it reportedly didn’t last long, if at all. De Cadenet revealed in the 2017 book It’s Messy: Essays on Boys, Boobs and Badass Women that there was a mutual attraction between them.

“We met when I was two months pregnant, 19 years old and married to another man [John Taylor of Duran Duran],” de Cadenet wrote. “Within minutes of first laying eyes on [Reeves], 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.”

De Cadenet wrote that Reeves, “a man with hardcore ethics,” didn’t get involved with her then but did go on a date with her after she divorced Taylor in 1997.

Jennifer Syme

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Reeves and Syme began dating in 1999; soon after, the pair announced they were expecting their first child. Tragically, their daughter, Ava, was stillborn at 8 months in January 2000. According to reporting from PEOPLE at the time, their relationship could not withstand the grief of losing their child, and they decided to split up weeks later but remained on good terms.

Tragedy struck again when, on April 2, 2001, just one day after seeing Reeves for lunch, Syme lost control of her car and died in an accident.

Claire Forlani

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The Matrix actor was linked to Forlani from 2004 to 2006, though he laughed off the rumors that the pair were engaged to the New York Daily News in 2006. “We’re good friends,” he said at the time.

Alexandra Grant

The actor is reportedly involved with Grant. The pair held hands while posing for photos at the LACMA Art + Film Gala,

Although neither have commented on the nature of their relationship, Reeves and Grant have known each other for quite some time, having collaborated first in 2011 on Reeves’ book Ode to Happiness. They worked together again in 2016 on his book, Shadows, which was illustrated by Grant. The also founded a publishing house together, X Artists’ Books, in 2017.

A source told PEOPLE after the couple’s red carpet debut in November 2019 that they “started dating earlier this year, but have wanted to keep it quiet.”

The source added, “Keanu wants to openly share his life with her. He is extremely happy and grateful to have Alex in his life.”

Following Grant’s debut with Reeves, she told Vogue that she felt mixed emotions about her decision to publicize her relationship.

“I think every single person I knew called me in the first week of November, and that’s fascinating, but the question I’ve been asking in all of this is: ‘What is the opportunity for good,'” she said.

The private twosome was also spotted holding hands in New York City in the summer of 2022 after attending a Broadway performance and strolling hand-in-hand while shopping on Fifth Avenue.