A Look Inside Keanu Reeves' Dating History: Every Woman the Super Private Actor Has Dated

Keanu Reeves sent fans into a tizzy on Nov. 2, 2019, when he stepped onto the red carpet for the LACMA Art + Film Gala presented by Gucci in Los Angeles with his rumored girlfriend, artist Alexandra Grant. Reeves, who is having a serious moment thanks to the John Wick franchise and parts in movies like Toy Story 4 and Always Be My Maybe, is notoriously private about his love life — and understandably so. While Reeves has dated A-list actresses, he has also experienced tragedy in his personal life.

Here, we take a look back at the actor’s romantic history to ask: Which lucky ladies have been able to call the Internet’s boyfriend their leading man?

Alexandra Grant

The 55-year-old actor is reportedly involved with 46-year-old Graham. The pair held hands while posing for photos at the LACMA Art + Film Gala, though neither has commented on the nature of their relationship. The pair have known each other for quite some time, having collaborated first in 2011 on Reeves’ book Ode to Happiness. They worked together again in 2016 on his book, Shadows, which is illustrated by Graham. The also founded a publishing house together, X Artists’ Books, in 2017.

A source told PEOPLE after the couple’s outing that they “started dating earlier this year, but have wanted to keep it quiet.”

The source added, “Keanu wants to openly share his life with her. He is extremely happy and grateful to have Alex in his life.”

Claire Forlani

The Matrix actor was linked to Forlani from 2004 to 2006, though he laughed off the rumors that the pair were engaged to the New York Daily News in 2006 saying, “We’re good friends.”

Jennifer Syme

Reeves and Syme began dating in 1999, and soon after, announced they were expecting their first child. Tragically, their daughter, Ava, was stillborn at eight months in January 2000. According to reporting from PEOPLE at the time, their relationship could not withstand the grief of losing their child, and they decided to split up weeks later, but remained on good terms.

Tragedy struck again when, on April 1, 2001, just one day after seeing Reeves for lunch, Syme lost control of her car and died in an accident.

Amanda de Cadenet

Reeves was linked to the ’90s personality, but it reportedly didn’t last long, if at all. de Cadenet revealed in her book, It's Messy: Essays on Boys, Boobs and Badass Women, that there was an attraction between the two. “We met when I was two months pregnant, 19 years old, and married to another man [John Taylor of Duran Duran] …” de Cadenet wrote. “Within minutes of first laying eyes on [Reeves], 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.” de Cadenet wrote that Reeves, “a man with hardcore ethics,” didn’t get involved with her then, but did go on a date with her after she divorced Taylor in 1997.

Sofia Coppola

Reeves dated the then up-and-coming director after meeting her on the set of Bram Stoker’s Dracula, which was directed by her father, Francis Ford Coppola. The pair reportedly dated briefly before splitting up in 1992.

Winona Ryder

The former co-stars never dated, but they may be technically married! Ryder told Entertainment Weekly that, while on the set of the 1992 film, Bram Stoker’s Dracula, the pair may have accidentally been wed for real by a Romanian priest. Ryder explained, “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.” The pair had a laugh about the revelation in the interview, which they did while promoting their recent rom-com Destination Wedding.

Jill Schoelen

The pair met when they were filming one of Reeves’ first films, Babes in Toyland, and were rumored to have dated for almost three years.