Despite being one of Hollywood’s most successful (and beloved) actors, Keanu Reeves has not had an easy life — far from it. At an early age, he experienced a string of losses and heartbreak that would forever affect his approach to relationships. 

As his career blossomed, Keanu’s personal life, which he has kept extremely private, was impacted by his fear of losing more people he loved, which made building a new, lasting connection difficult. That all changed, however, when the right person came along. When Reeves met Alexandra Grant (a visual artist specializing in text-based paintings), she gave him the strength to take a chance on love again and proved that finding The One can happen at any age.

Here’s what we can learn from Keanu Reeves and Alexandra Grant’s relationship:

Keanu Reeves’ early years were marred by tragedy 

When the Matrix star was just three years old, his parents divorced and his father left the family in New York to move back to his native Hawaii.

Reeves would see his dad for the last time when he was 13. “On our last day we sat on the veranda and stared at the dark sky,” he recalled of his final holiday in Hawaii.

The next day he brought us to the airport. Then we didn’t hear anything from him for 10 years. No calls, no letters, nothing.

Keanu Reeves

Noting that “neither the police nor hospitals were able to find Dad,” the actor revealed that when Reeves Sr. did eventually reappear a decade later, they “no longer had any contact.”  

Jump to around 1991 and Keanu had to endure yet another family hardship when his younger sister, Kim, was diagnosed with cancer. As Woman’s Day Australia reported in 1999, he became her primary caregiver and “lovingly supported Kim since she was diagnosed with lymphatic cancer more than 10 years ago.”

Opening up about her battle with leukemia, Kim told the outlet, “Keanu helped me so much through my illness. When the pain got really bad, he would sit with me and hold my hand,” she continued. “He was supporting me and comforting me all the time, even when he was away.”

The blows just kept coming when, in 1993, Reeves lost his best friend, actor River Phoenix, to an overdose. Reeves was shooting Speed at the time and co-star Sandra Bullock recalled how pain seemed to emanate from him. “I think that he has gone through a lot even though he doesn’t let on about it,” she told Télé 7 Jours in 1994. “I think he hides a great pain.” 

Reeves himself eventually addressed Phoenix’s death, telling Us Weekly in 1995, “I was terribly, terribly, terribly sad. Incredibly sad. And, um, I miss him very much.” That feeling, unfortunately, never went away. In 2019, the loss of his friend still weighed on him as he told the Irish Times, “[River was] definitely my closest friend from that era […] Yeah, I miss him.” 

The loss of a child changed him forever 

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Keanu Reeves’ tragic real-life story continued to become even more heartbreaking through the late ‘90s. In 1998, he met Jennifer Syme (a personal assistant to director David Lynch) at a promo party for his band, Dogstar. The pair hit it off and were soon ready to start a family. Syme became pregnant, but on Christmas Eve 1999, she gave birth to a stillborn daughter, Ava Archer Syme-Reeves.

The couple couldn’t work past the loss and split up only a few weeks later. Then, in April 2001, a 28-year-old Syme died when she got behind the wheel while under the influence, hit a row of parked cars and was ejected from the driver’s seat. 

Grief “never ends” and it’s hard to overcome

The loss of his first (and only) child followed closely by the death of the woman he was so ready to build a life with changed Reeves’ approach to relationships forever.

Grief changes shape, but it never ends. People have a misconception that you can deal with it and say, ‘It’s gone, and I’m better.’ They’re wrong. When the people you love are gone, you’re alone.

Keanu Reeves to Parade

Keanu added that he still thinks about “what the present would be like if they were here.” 

Over time, Reeves eventually learned to pull strength from his experiences — “Much of my appreciation of life has come through loss,” he admitted — but everything he went through had a lasting effect on his ability to open up and build meaningful connections. “I’m trying not to be alone so much. And, man, it’s a struggle,” he told Parade.

I want to get married. I want to have kids. That’s at the top of the mountain. I’ve got to climb the mountain first. I’ll do it. Just give me some time.

Keanu Reeves

The right person can come along at any age

MALIBU, CALIFORNIA – JUNE 06: (L-R) Alexandra Grant and Keanu Reeves attend the Saint Laurent Mens Spring Summer 20 Show Photo Call on June 06, 2019 in Malibu, California. (Photo by Neilson Barnard/Getty Images)

While working on himself, Keanu Reeves didn’t have any more children and, eventually, appeared to pretty much give up on love. In 2017, when Esquire asked the John Wick star if he’d like to settle down, he replied, “It’s too late. It’s over. I’m 52,” he proclaimed, adding, “I’m not going to have any kids.” 

That attitude soon changed, however, thanks to Alexandra Grant. While it’s not clear when the pair first began dating —  Jennifer Tilly told Page Six she learned of their union around mid-2018 — what is clear is that Alexandra was just the person Keanu needed. 

Keanu and Alexandra first met at a dinner party in 2009, but had a working relationship for years before making their official couple debut on the LACMA Art + Film Gala red carpet in November 2019.

People were surprised to see him with a woman like Alexandra, who does not fit the expectations that the public has when it comes to celebrity girlfriends. In fact, Alexandra herself was very much aware of the impression she made.

I’m a 6ft 1 in woman with white hair. You know, the idea of fitting in… If I wanted to look like Kim Kardashian, I would have to have surgery removing about a foot off my legs.

Alexandra Grant to British Vogue

At 46, she wasn’t as young as the world had expected her to be. With grey hair she had embraced since her 20s, Alexandra’s unconventional, yet captivating, appearance shocked the world.

A shared passion is a great building block

Keanu Reeves and Alexandra Grant (credit: Credit:
Pierre Suu / Contributor)

Before they began dating, Keanu Reeves and Alexandra Grant built a strong connection on a shared passion: art and literature. In 2011, they worked together for the first time when they published Ode to Happiness, “a grown-up’s picture book” that paired drawings by Grant with a text by Reeves. In 2015, they published Shadows, which again featured the actor’s writing, this time paired with photos of him taken by Grant.

Their collaborations were so fulfilling that, in 2018, they decided to become business partners and launched X Artists’ Books, which the New York Times described as a “small press […] producing aggressively esoteric titles of the kind that wouldn’t fly at larger imprints.” As the outlet noted, they make all of their business decisions together, including finding everything they publish. 

Once romance began to bloom, this positive teamwork translated to their personal life. As one insider told Closer Weekly in May 2020, “They occasionally disagree on minor things but never argue. Whenever you’re around Keanu and Alexandra you get a sense of calmness — there’s just something about them that puts you at ease.” 

As for the book that sparked it all, Alexandra told British Vogue in March 2020 that Ode to Happiness was actually “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,” she revealed.

Overcoming hardship is easier as a team 

Overcoming loss will never be an easy process, but having someone loving by your side can make all the difference. Although neither Reeves nor Grant have publicly opened up about their love, according to insiders, the actor has experienced the healing power of a strong union first-hand. 

As one source told Life & Style in 2019, “Keanu was so traumatized by [Jennifer Syme’s] death that there were times when he couldn’t get out of bed in the morning,” but “everything changed” when he met Grant.

“He was in such a dark place for so long, but Alexandra’s positive outlook and support have played a huge part in helping him turn his life around,” the insider explained, noting that communication has been a major key to their success.

“She’s kind, warm and spiritual, just like Keanu, and a great communicator. She’s one of the few people who’s managed to get Keanu to open up about his emotions and past,” they concluded. 

Actress Jennifer Tilly went as far as to say the following:

They’re sort of the perfect couple. I think everybody wishes that they had something like that. It’s not a razzle dazzle Hollywood romance.

Jennifer Tilly to Page Six

Asked if she thought her friends would ever tie the knot, Tilly told Page Six, “I don’t know that doesn’t seem very hip and bohemian, does it? They’re artists. They’re just going to do what they do.”

Keanu’s choice was perceived to be unconventional

It’s clear that Keanu Reeves and Alexandra Grant are playing by their own rules — and it’s working. Following a heartbreaking string of losses, Keanu appeared to close his heart off almost completely but all it took was the right person to help him take the next step. As their connection blossomed out of a shared passion, Alexandra’s enthusiasm, love and support turned out to be just what Reeves needed to try his hand at love again.

So much so that, in November 2019, he felt confident enough to walk the red carpet with a partner for the first time in three decades(and pretty much broke the Internet in doing so). It just goes to show that love really is an unrivaled healer.

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