Keanu Reeves’ Romantic History: Every Star He’s Dated Over The Years

In our favorite films, Keanu Reeves has romanced beauties like Sandra Bullock and Winona Ryder. But who has Keanu loved offscreen?

Keanu Reeves is one of Hollywood’s most famous leading men. But his personal life still remains somewhat a mystery. That’s why fans absolutely flipped out when he went public with his current romance — they weren’t used to seeing him with anyone! His relationship with artist Alexandra Grant has shown that in 2020, the Bill & Ted Face The Music star, 56, is anything but “Sad Keanu” anymore.

Onscreen, Keanu has paired up with some of the most gorgeous leading ladies in the industry, like Sandra Bullock, twice, in Speed and The Lake House, Diane Keaton in Something’s Gotta Give, and Ali Wong in Always Be My Maybe. Offscreen, his track record is just as enviable. Take a look at the actor’s romantic history and see the famous beauties he’s dated over the years:

Alexandra Grant

Keanu and Alexandra went public with their relationship in November 2019. The couple, who run a publishing house called X Artists’ Books together, have been close friends for decades, and have actually been dating “for years,” her friend, actress Jennifer Tilly, revealed in February 2020. Alexandra, 46, told British Vogue in March that “every single person I knew” called her when they saw her walk a red carpet with Keanu for the first time. Since then, they’ve hit plenty of events together, and she’s even traveled with him to Berlin while he films The Matrix 4.

Claire Forlani

Keanu and Meet Joe Black star Claire Forlani, 48, were linked from 2004 to 2006, and rumors even swirled that the two were engaged. Keanu, according to one report, popped the question to Claire by getting down on one knee in the middle of Wolfgang Puck’s Hollywood restaurant Cut. Unfortunately for shippers, that wasn’t true. He laughed off the engagement — and even romance — speculation in a 2006 interview with The New York Daily News, saying that he and Claire were “good friends.”

Jennifer Syme

Keanu began dating Lost Highway actress Jennifer Syme in 1998. The couple announced they were expecting their first child together the following year. Tragically, their daughter, Ava Reeves, was stillborn at eight months in January 2020, and they unfortunately ended their relationship after not being able to withstand the grief of losing their child. They remained on good terms, though. Shockingly, Jennifer died in April 2001 at the age of 28 after losing control of her car. She and Keanu had met up for lunch just one day prior.

Amanda de Cadenet

Keanu was linked to Amanda de Cadenet in the late 1990s, but according to The Word host, it didn’t last long. Oh — and it was messy. In her memoir, It’s Messy: Essays on Boys, Boobs and Badass Women, Amanda wrote, “We met when I was two months pregnant, 19 years old, and married to another man [John Taylor of Duran Duran]. Within minutes of first laying eyes on [Keanu], 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.” However, Keanu, “a man with hardcore ethics,” didn’t ask her out on a date until after her divorce in 1997. They’ve remained good friends since.

Sofia Coppola

Keanu’s relationship with then-burgeoning director Sofia Coppola was short, but sweet. The couple met when Keanu starred in her father, Francis Ford Coppola‘s film Bram Stoker’s Dracula in 1991. They briefly dated before splitting up the following year. Sofia, now 49, would go on to marry fellow director Spike Jonze. After their divorce, she later married Phoenix lead singer Thomas Mars.

Winona Ryder

Keanu and Winona Ryder never really dated — but they could technically be married! Winona, 48, told EW in 2018 that their characters in Bram Stoker’s Dracula were wed by an actual priest. “We actually got married in Dracula. No, I swear to god I think we’re married in real life. 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,” she joked in a joint interview with Keanu while promoting their romcom Destination Wedding. The best part? They said their vows on Valentine’s Day!