Inside Keanu Reeves’ troubled relationships now that he’s finally found love: a timeline

After years of heartbreak, missed opportunities, and personal tragedy, Keanu Reeves has finally found love with his "best friend".
After years of heartbreak, missed opportunities, and personal tragedy, Keanu Reeves has finally found love with his “best friend”. Picture: Getty

Keanu Reeves is not your typical celebrity in Hollywood.

The Matrix, Speed, and John Wick actor has strived to keep his personal life private over his entire career in the spotlight.

It’s a challenging juggling act of preserving his fame and starring in international blockbuster films, all while keeping the media at bay.

When it concerns the romantic relationships and love life of Keanu Reeves, there is restricted information accessible concerning his previous companions over the years.

The public knows what tragedy-stricken and troubled relationships Keanu has likely been in, which is why he has kept his private life so private.

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  • The situation has now been changed, with the arrival of his new partner which the actor from Point Break has publicly announced.

    On Saturday, Keanu showcased his affectionate relationship with his new partner Alexandra Grant at the Museum of Contemporary Art Gala in Los Angeles.

    It seems that finally after years of heartbreak, missed opportunities, and personal tragedy that he has found love with his “best friend”.

    However, with whom else has Keanu been involved romantically over the years? Let’s delve into the past and explore the love life of this renowned actor from Hollywood.

    Alexandra Grant

    Keanu Reeves has finally found love with his "best friend". (Photo by Elyse Jankowski/FilmMagic)
    Keanu Reeves has finally found love with his “best friend”. (Photo by Elyse Jankowski/FilmMagic). Picture: Getty

    Keanu Reeves’ present partner is visual artist Alexandra Grant, whom he has been in a relationship with since 2019.

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    The pair’s first public outing as a couple took place in that same year, following a clandestine romance for a few months.

    Keanu initially encountered Alexandra in 2009, and they have regularly collaborated on a range of undertakings.

    In 2011, Alexandra and Keanu published two illustrated books in Happiness To Ode. In 2016, they released Shadows. They also co-founded X, a publishing company, in 2017, which they co-own.

    Through their collaboration, they developed a strong bond and eventually Keanu and Alexandra progressed to a romantic relationship.

    Keanu recently provided a unique glimpse into their love story when he mentioned his “final moment of happiness” in People Magazine, stating:

    It was so lovely to be together. We had such a wonderful feeling. We were giggling, laughing, and smiling. We felt a strong connection. We were lying in bed. A few days ago, we were a happy couple with my beloved honey.

    Jill Schoelen

    Keanu Reeves met Jill Schoelen on one of his early films.
    Keanu Reeves met Jill Schoelen on one of his early films. Picture: NBC

    While shooting the film Babes In Toyland in 1986, Keanu crossed paths with actress Jill Schoelen, who became one of his first romantic companions.

    The couple were on-screen romantic partners that eventually evolved into an off-screen relationship, and lasted for three years before breaking up.

    Jill then started dating Brad Pitt, who were betrothed for a brief time.

    Winona Ryder

    Winona Ryder and Keanu Reeves (pictured here in 2018) first met in 1992. (Photo by Kevin Winter/Getty Images)
    Winona Ryder and Keanu Reeves (pictured here in 2018) first met in 1992. (Photo by Kevin Winter/Getty Images). Picture: Getty

    One of Keanu’s stranger relationships was with actress Winona Ryder, after he confessed that they may’ve been married for nearly thirty years.

    The two Hollywood stars met after starring in Dracula, a 1992 film adaptation of Bram Stoker’s novel, where their characters were married, even though they may have realized that the ceremony may have been more legitimate.

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    In a recent interview, Keanu explained that we performed a complete marriage ceremony with actual priests. So, Winona says we are married under the watchful eyes of God.

    Winona has remarked about their ‘wedding’ in an interview with Entertainment Weekly in 2018, stating: “We actually tied the knot in Dracula.”

    I think we’re married, so I did the whole thing and the director shot us with the real Romanian priest, Francis. I swear to God, I don’t think we’re actually married in real life.

    Although their marriage may not actually be a sham, they’ve never expressed any romantic feelings for each other but remain good friends.

    Sandra Bullock

    Keanu Reeves and Sandra Bullock at the premiere of Speed in 1994. (Photo by Ron Galella/Ron Galella Collection via Getty Images)
    Keanu Reeves and Sandra Bullock at the premiere of Speed in 1994. (Photo by Ron Galella/Ron Galella Collection via Getty Images). Picture: Getty

    Sandra Bullock and her co-star Keanu Reeves received high praise from cinema-goers for their remarkable chemistry in the 1994 high-octane action thriller, Speed. The film garnered rave reviews upon its release.

    The gossip machine went into overdrive as there was a little more happening with their chemistry than initially apparent, well, it transpires.

    Both stars confessed they had a crush on one another during the shoot, confirming their affections on separate interviews with Ellen DeGeneres.

    “It was clear that she was unaware of my feelings for her! It dawned on me that Keanu and I would never have a romantic relationship, despite our mutual crushes. However, we were not proactive enough to move the situation forward.”

    Amanda of Cadenet

    Amanda De Cadenet was pregnant and married when she met Keanu. (Photo by SGranitz/WireImage)
    Amanda De Cadenet was pregnant and married when she met Keanu. (Photo by SGranitz/WireImage). Picture: Getty

    In the 1990s, Keanu had a public romance with Amanda de Cadenet, a British socialite and presenter-turned-photographer, for a brief period of time.

    But there was a huge problem: at the time, Amanda was pregnant and married to Duran Duran bassist John Taylor no less.

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    In her book “Badass Women and Messy Boys: It’s all about Boobs”, Amanda opened up about her whirlwind romance with Keanu, when we met I was 19 years old and two months pregnant.

    I was pleasantly surprised by a man I had just met, who quickly captivated my attention. “I can’t help but wonder how many women he has impregnated,” I thought to myself, as I locked eyes with him within the first few minutes.

    Once her divorce from John Taylor was finalized, their brief relationship came to an end because Keanu was a “man with strong moral principles”, although they would remain in contact.

    Jennifer Syme

    Keanu and Jennifer were in a whirlwind romance before tragedy struck.
    Keanu and Jennifer were in a whirlwind romance before tragedy struck. Picture: All Action
    Keanu being comforted at Jennifer's funeral. (Photo by Bauer-Griffin/GC Images)
    Keanu being comforted at Jennifer’s funeral. (Photo by Bauer-Griffin/GC Images). Picture: Getty

    During the late 1990s, Jennifer Syme, an assistant production Hollywood, began dating Keanu Reeves after they met at an after-party for Dog Star.

    Following their initial encounter, they conceived their first offspring shortly thereafter and developed a deep affection for each other almost immediately, establishing an instant bond.

    Unfortunately, it would signify the start of a period of unimaginable sorrow for Keanu, one that took him many years to conquer.

    On Christmas Eve in 1999, they discovered that their baby had been stillborn after eight months of Jennifer’s pregnancy, when they had been eagerly anticipating the arrival of their child.

    Suffering from post-natal depression and the grief of losing their child, the relationship couldn’t handle it so Keanu and Jennifer eventually split.

    Shortly after their encounter with Keanu, Jennifer tragically passed away in a car accident in 2001. Up until her unfortunate demise in 2001, they maintained a strong friendship and were on the brink of resolving their differences.

    After years of personal struggle, he has finally found love, and we are so happy and grateful that he has remained grounded and humble throughout it all.

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