Keanu Reeves, the beloved Hollywood icon known for his roles in blockbuster franchises like The Matrix and John Wick, has long been a heartthrob in the entertainment industry. Over the years, his charm, humility, and on-screen charisma have not only won over millions of fans but also caught the attention of some of Hollywood’s most prominent leading ladies. From playful flirtations to rumored romances, Keanu has shared undeniable chemistry with co-stars Charlize Theron, Sandra Bullock, and Winona Ryder, sparking fascination and speculation among fans. Let’s dive into the stories of how these celebrated actresses have openly admired—or even flirted with—Keanu Reeves, making him the subject of affection both on and off the screen.

Charlize Theron: A Sizzling On-Screen Connection

Charlize Theron and Keanu Reeves first crossed paths while filming the 1997 horror fantasy The Devil’s Advocate, where Theron played Mary Ann Lomax, the wife of Keanu’s character, Kevin Lomax. Their on-screen chemistry was electric, with Theron’s portrayal of a woman unraveling under supernatural forces complementing Keanu’s intense performance as a lawyer facing moral dilemmas. The pair reunited in 2001 for the romantic drama Sweet November, a film that further showcased their ability to portray deep emotional connections. In Sweet November, Theron’s character, Sara Deever, a free-spirited woman battling illness, transforms the life of Keanu’s workaholic Nelson Moss, leading to a poignant love story.

Keanu has spoken highly of their dynamic, once describing their on-screen chemistry as “f–king hot” during a 2000 press junket for The Gift. He elaborated, “We get along really well. We’re friends, we know each other, but there’s something that happens when we act together that’s very different than how we are in life. It’s the oddest thing.” Fans certainly agreed, with many noting the palpable sparks between the two. Their connection wasn’t just limited to the screen—rumors of a brief romance surfaced around 2009-2010, fueled by a 2010 sighting in Beverly Hills where the two were spotted sharing an intimate embrace after dinner, as reported by the Daily Mail. A source told Hollywood Life at the time, “Keanu and Charlize were having a great time. They were constantly laughing, almost disrupting other tables with how loud they were. They were wrapped up in each other’s conversation.”

Charlize herself has shown her admiration for Keanu publicly. On his 56th birthday in September 2020, Theron posted a heartfelt message on social media, writing, “I love this handsome human so much!” The gesture won over Keanu’s fans, who appreciated her genuine affection for the actor. While the rumored romance was never confirmed, their decades-long friendship remains a testament to their mutual respect and chemistry, leaving fans to wonder what might have been.

Sandra Bullock: A Missed Romantic Opportunity

Sandra Bullock and Keanu Reeves first captivated audiences in the 1994 action thriller Speed, where Bullock played Annie, a quick-witted bus passenger, and Keanu portrayed Jack Traven, a daring cop. The film’s high-stakes tension was balanced by the undeniable chemistry between the two leads, with their playful banter and shared moments of vulnerability winning over audiences. They reunited in 2006 for the romantic fantasy The Lake House, a story of two people connecting across time through a magical mailbox, further showcasing their ability to portray longing and love.

Off-screen, their connection was just as compelling. During a 2019 appearance on The Ellen DeGeneres Show, Sandra Bullock admitted to having a massive crush on Keanu while filming Speed. “I think about how sweet Keanu Reeves was and how handsome he was,” she confessed, adding, “It was hard for me to really be serious because I would just giggle.” She revealed that Keanu was equally smitten, noting that he later told her he had a crush on her too—but neither acted on their feelings because “there’s just something about me that I guess he didn’t like,” she quipped. Keanu, appearing on the same show a few months later, confirmed his feelings, saying, “She obviously didn’t know I had a crush on her either.” The revelation left fans lamenting the missed opportunity for a real-life romance between the two.

Despite never dating, Sandra and Keanu have maintained a close friendship over the years. In a 2021 interview with the Philippine Daily Inquirer, Sandra described Keanu as “a guy who is friends with every woman he’s ever dated,” emphasizing his kind nature. Their bond, built on mutual admiration and respect, has endured for over three decades, making them one of Hollywood’s most beloved “what-if” pairings.

Winona Ryder: A Playful “Marriage” and Lasting Friendship

Winona Ryder and Keanu Reeves share a unique and endearing connection that dates back to their first meeting at the 1989 American Spirit Awards. Their on-screen collaborations began with the 1992 gothic horror Bram Stoker’s Dracula, where they played lovers in a wedding scene officiated by a real Romanian priest. The authenticity of the ceremony led Winona to jokingly claim they might be legally married. In a 2018 interview with Entertainment Weekly, she reminded Keanu, “We actually got married in Dracula. No, I swear to God, I think we’re married in real life.” Keanu played along, later telling PEOPLE, “Winona is a lovely person and a talented actress. I think we make a good couple.”

The pair’s chemistry shone again in the 2018 romantic comedy Destination Wedding, where they played cynical wedding guests who unexpectedly fall for each other. Winona has been open about her admiration for Keanu, revealing in a 2018 interview that she had a “big, healthy crush” on him since their first meeting. “We’ve been friends for a long time,” she told Vanity Fair, praising his understated acting style: “It’s like what Katharine Hepburn said about Spencer Tracy—‘There’s no embroidery. He just does it.’”

Rumors of a romance between Winona and Keanu circulated in the late 2000s, with WhosDatedWho reporting a possible fling around 2008. While neither confirmed the rumors, their playful dynamic and genuine friendship have kept fans intrigued. Winona’s lighthearted claim of being “married” to Keanu, combined with their effortless on-screen rapport, has made them a fan-favorite duo, with many hoping for another collaboration in the future.

Keanu’s Timeless Appeal

Keanu Reeves’ appeal goes beyond his striking looks and acting talent. Known for his humility, kindness, and private nature, he has earned a reputation as one of Hollywood’s most genuine stars. His interactions with Charlize Theron, Sandra Bullock, and Winona Ryder highlight not only his on-screen charisma but also his ability to form deep, meaningful connections off-screen. Whether it’s Theron’s flirty embraces, Bullock’s giggly confessions, or Ryder’s playful “marriage” claims, these women have all been drawn to Keanu’s unique charm.

As of May 10, 2025, Keanu remains in a committed relationship with artist Alexandra Grant, a partnership that has been public since 2019 and is reportedly rooted in a deep friendship that began years earlier. Despite his taken status, the stories of his flirtatious encounters with Hollywood’s leading ladies continue to captivate fans. Keanu’s ability to inspire such affection from co-stars like Theron, Bullock, and Ryder underscores why he remains an enduring icon—both in cinema and in the hearts of those who know him best.