Keanu Reeves is a private man. Though he's excellent at keeping his love life under wraps, there's enough information to piece together his romantic timeline. Heartbreak and tragedy haven't been enough to keep Reeves from falling in love again and again.
Reeves met acclaimed director Sofia Coppola while working with her father, Francis Ford Coppola, on the film Bram Stoker's Dracula. The couple didn't last long, however. Less than a year after they began dating, the two broke up.
Jennifer Syme was an actress and director's assistant who met Reeves at a party for his band, Dogstar, in 1998. The movie star instantly fell for Syme and soon, she was pregnant. Sadly, their daughter, Ava Archer Syme-Reeves, was stillborn. It's believed that the grief of losing a child, as well as postpartum depression, led to a break up. Still, Reeves and Syme remained friends, but that was short-lived as Syme died in a car accident while leaving a party thrown by rocker Marilyn Manson.
The most recent addition to Reeves' conquests is artist Alexandra Grant. Grant and Reeves became romantically linked after Reeves brought Grant as his date to a red carpet event. What really drove people to believe that this was a romantic liaison rather than a platonic friendship was the way the couple held hands. The two have known each other for years and have even worked together. Together, Reeves and Grant have published two books, and they started a publishing company. It's still not clear if Reeves and Grant are just friends, or if they are dating.
There have been a lot more rumors about who Reeves is actually dating than there's been real information. For instance, Reeves is often romantically linked to Sandra Bullock in the tabloids, but the stars never dated. Bullock admitted in an interview that she did have a crush on Reeves back when they co-starred in Speed, which led Reeves to admit that he'd also had a crush on her. Obviously, the timing was never right with this couple.
Similarly, Winona Ryder revealed in an interview that she also had a crush on Reeves while they filmed Dracula together, but she'd never acted on it. Reeves, just like with Bullock, shared that he'd also had a crush, though he'd never said anything about it.
In those examples, there was clearly a reason for romantic rumors to spread. The feelings were there, but no one acted on them. Some publications, however, feel the need to make up intrigues where there are none. In 2018, NW reported that Angelina Jolie was settling down with Reeves. Gossip Cop reached out to one of Jolie's reps, who informed us the two weren't in a relationship. This rumor has been busted a number of times since.
Again in 2018, a tabloid erroneously linked Reeves with a famous leading lady. Life & Style claimed Reeves and Halle Berry were in a "hot romance," but Gossip Cop was able to easily disprove this rumor. Over a year later, it's clear the claim was totally made up, and Reeves seems very happy keeping his private life private.
Gossip Cop has determined this story is accurate to the best of our ability.