Though he’s immortalized on screen, in real life, mortality has been a merciless foe to Keanu Reeves, who spent years lamenting the loss of his baby Ava, her mother, a best friend, and almost his sister–who says he’s her “prince.”

After years of trauma, the shy and soft-hearted star said he was feeling “alone,” until he found–as his alter ego Ted would say–his “righteous babe,” Alexandra Grant. And, an insider says the woman is changing the status of the lifelong bachelor, who is expected to propose.

Keanu Reeves, now 58, made his feature film debut at 22 in the 1986’s Youngblood, a sports drama also starring Rob Lowe and the late Patrick Swayze.

His breakthrough role came in 1989 with Bill and Ted’s Excellent Adventure, a sci-fi comedy with outrageous catch phrases–like “righteous babe”–that still influence pop culture.

“I don’t want to be super famous, man,” Reeves told New York’s Newsday in 1991. “That would be awful.”

But the world had other plans for the handsome dark-haired actor.

One of Hollywood’s most sought-after actors, the Beirut-born Canadian then had massive success with appearances in several films like Point Break (1991) and Speed (1994), establishing himself as an action hero.

But then, in 1991 his younger sister Kim–a former actor and writer–was diagnosed with leukemia, a life-threatening blood cancer, which shook the ground on which he stood.

“She was always there for me, you know. I will always be here for her,” said the star, who at 23 became Kim’s stay-at-home nurse – at the peak of his acting career.

“My brother is my prince,” Kim tells People. “He listens to every word, to every comma after every word, that you are saying.”

Kim, who’s now 56 and has recovered, has built a private foundation to help others on their journey with cancer. Reeves is her silent partner in the mission.

However, while his sister lives, other losses kept rolling in.

Equally painful was the 1993 drug overdose of 23-year-old River Phoenix, his close friend, and co-star in the 1991 film My Private Idaho.

Reeves said: “I’ve always loved you, River. River is my best friend, and I don’t have many of them,” said Reeves, years ago, of the young actor he called his “brother.”

At the time of River’s death, Sandra Bullock, who co-starred with Reeves in Speed, revealed that he was hiding a deep sadness. She said, “I think Keanu has gone through a lot even though he doesn’t let on. He hides a great pain.”

For a moment, which lasted from 1998 to 2000, Reeves was handed a brief reprieve.

In 1998–one year before he played the formidable warrior in the award-winning Matrix–the brooding actor met a young woman, Jennifer Syme, the former assistant to Twin Peaks director David Lynch.

The pair’s relationship, and then pregnancy, became fodder to the media and troublesome to the notoriously shy star.

Swirling rumors proved to be true when on December 24, 1999, Syme gave birth only eight months into her pregnancy, and baby Ava was stillborn. The grief was too much for the couple to resolve, and their relationship ended, reconciling to become a close friendship a few weeks later.

Only months after burying Ava, Syme, 29, was killed when her car sideswiped three parked cars, rolled over several times, and tossed her from the vehicle she was operating. According to reports, Syme, who died instantly on April 4, 2001, was not wearing a seatbelt and was under the influence of alcohol at the time.

Trying to overcome his losses, he channeled his grief into his character of the unforgiving assassin in the John Wick franchise.

“I thought it was one of the foundations of the role. I love his grief,” he said. “I relate to that, and I don’t think you ever work through it…Grief and loss don’t ever go away.”

Still struggling, Reeves, an introvert, admitted he didn’t want to live in sadness and consciously put effort into reclaiming his life.

“When the people you love are gone, you’re alone…I miss all the great things that will never be. It’s not fair! It’s absurd. I think, after loss, life requires an act of reclaiming. You have to reject being overwhelmed. Life has to go on.” The star continued, “I’m trying not to be alone so much, and man, it’s a struggle. 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.”

And recently, Reeves revealed he scaled that mountain and at the top, he found artist Alexandra Grant, 50. Though the couple tends to be very private about their relationship, Reeves couldn’t help but gush over his beautiful love.

While promoting John Wick: Chapter 4, released in late March 2023, the actor spoke with People magazine and shared some sweet moments he had with his new belle.

When asked about his last moment of bliss, Reeves replied: “A couple of days ago with my honey. We were in bed. We were connected. We were smiling and laughing and giggling. Feeling great.” He continued, “It was just really nice to be together.”

Though it’s unclear exactly when the two met, according to Reeve’s friend, actor Jennifer Tilly, the two have been together much longer than fans realize.

“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?’” said Tilly, 64.

The relationship between Reeves and Grant relationship dates back to their debut book, “Ode to Happiness” that was published in 2011. The book is an adult picture book with illustrations by Grant and text from the actor.

Then in 2016, Reeves and Grant posed at the event for UNAIDS Gala during Art Basel 2016 in Basel, Switzerland and in the same year, they collaborated on a second title, “Shadows.” This art book features 54 images, captured by Grant that are based on the movements of Reeves.

Years later, the couple went public at the 2019 LACMA Art + Film Gala, and then in June 2022, the adorable lovers were seen holding hands at a Broadway performance.

A source close to Reeves said the actor was ready to propose to Grant, who he has been with five years.

Life & Style magazine reports, “Keanu isn’t hiding the fact that he’s going to propose to Alexandra. 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 continued, “Keanu and Alexandra have both been in relationships before, but this is by far the easiest. They just flow well together, they mesh perfectly…Maybe it’s because they’re mature, stable and know what they want from life. There’s no drama. And of course, they love each other. He adores Alexandra.”

 

We hope there is a proposal, and we are so excited to hear more about Keanu Reeves and Alexandra Grant!

Keanu Reeves has had so many struggles through his life and through it all, he’s been a pillar of support for those he loves and others with his charity work. He deserves the loving wife and children that he wants, and we can’t wait for more information on the gorgeous couple!

If Reeves does propose, how do you think he’ll do it?