Keanu Reeves’ Dating History: A Look Back at the Actor’s Relationships and Flings

Credit: Matt Baron/Shutterstock; Shutterstock; RAMEY PHOTO AGENCY/MEGA; Shutterstock

Keanu Reeves' Dating History: A Look Back at the Actor’s Relationships and Flings

Everyone deserves to find love, especially Keanu Reeves. Reeves is a recognizable and adored star in Hollywood who has appeared in countless high-profile films, from Toy Story 4 to the Matrix franchise. The celebrated actor has even been dubbed “the Internet’s boyfriend,” which is a title he was completely unaware of until June 2019. Despite the world’s intrigue with Revees, the Always Be My Maybe actor has managed to keep things relatively private, especially as it pertains to who he dates. He was last reported to be dating actress China Chow in 2008, but Reeves more recently sparked interest in his romantic life once again when he stepped out holding hands with Alexandra Grant at the LACMA Art + Film Gala in November 2019. The Constantine actor has been friends with Grant for years after they first met in 2009 at a dinner party. “It wasn’t a secret,” an insider told Us Weekly of the pair’s romance in November 2019. “They have been dating since at least [the] summer of 2017.” Reeves has never been married, but he opened up about the idea of settling down during an interview with Parade in 2006. “I’m trying not to be alone so much,” he told the magazine. “And man, it’s a struggle. I want to get married. I want to have kids. That’s at the top of the mountain. I’ve got to climb the mountain first. I’ll do it. Just give me some time.” [jwplayer tCcvpqs0-l3ahXupL] Reeves also mentioned his “vagabond” lifestyle, where he explained to the publication how “there is a bit of the gypsy” in him. He argued that “living that way seemed to make sense” for him. “I couldn’t settle down. I liked going to new places — renting apartments, staying in hotels. Then I turned 40,” he continued. “That birthday is hard, perhaps because, you know, you’re grown-up. So now it’s a makeover for me. I have bought my first house. I wanted a home.” Scroll down to take a closer look at who Reeves has been linked to over the years.

Credit: Matt Baron/Shutterstock; Shutterstock; RAMEY PHOTO AGENCY/MEGA; Shutterstock

Keanu Reeves' Dating History: A Look Back at the Actor’s Relationships and Flings

Everyone deserves to find love, especially Keanu Reeves. Reeves is a recognizable and adored star in Hollywood who has appeared in countless high-profile films, from Toy Story 4 to the Matrix franchise. The celebrated actor has even been dubbed “the Internet’s boyfriend,” which is a title he was completely unaware of until June 2019. Despite the world’s intrigue with Revees, the Always Be My Maybe actor has managed to keep things relatively private, especially as it pertains to who he dates. He was last reported to be dating actress China Chow in 2008, but Reeves more recently sparked interest in his romantic life once again when he stepped out holding hands with Alexandra Grant at the LACMA Art + Film Gala in November 2019. The Constantine actor has been friends with Grant for years after they first met in 2009 at a dinner party. “It wasn’t a secret,” an insider told Us Weekly of the pair’s romance in November 2019. “They have been dating since at least [the] summer of 2017.” Reeves has never been married, but he opened up about the idea of settling down during an interview with Parade in 2006. “I’m trying not to be alone so much,” he told the magazine. “And man, it’s a struggle. I want to get married. I want to have kids. That’s at the top of the mountain. I’ve got to climb the mountain first. I’ll do it. Just give me some time.” [jwplayer tCcvpqs0-l3ahXupL] Reeves also mentioned his “vagabond” lifestyle, where he explained to the publication how “there is a bit of the gypsy” in him. He argued that “living that way seemed to make sense” for him. “I couldn’t settle down. I liked going to new places — renting apartments, staying in hotels. Then I turned 40,” he continued. “That birthday is hard, perhaps because, you know, you’re grown-up. So now it’s a makeover for me. I have bought my first house. I wanted a home.” Scroll down to take a closer look at who Reeves has been linked to over the years.

Credit: Shutterstock

Jill Schoelen

Reeves was rumored to have dated his Babes in Toyland costar for three years after meeting on the 1986 film’s set. After they parted ways, Schoelen dated Brad Pitt and they were engaged for three months in 1989.

Credit: Shutterstock (2)

Sofia Coppola

The Bling Ring filmmaker briefly dated the A-list actor in 1992 after he was directed by her father, Francis Ford Coppola, in Bram Stoker’s Dracula.

Credit: RAMEY PHOTO AGENCY/MEGA

Jennifer Syme

Reeves’ relationship with Syme is his most notable, but it’s also his most tragic. Their romance began in 1998 and by 1999, the Ellie Parker actress was expecting the pair’s child. Their daughter, Ava, was stillborn in December 1999 and the couple eventually called it quits in 2000. One year later, Syme died when she was involved in a traffic collision.

Credit: Shutterstock

Claire Forlani

Reeves was rumored to have dated the Meet Joe Black actress from 2004 to 2006. However, when asked by the New York Daily News about their romance in 2006, he laughed off the concept. “We’re good friends,” he stated.

Credit: Shutterstock

Winona Ryder

The Knock Knock star was never in an official relationship with Ryder, but the Stranger Things actress revealed that the costars may have been mistakenly married while on the set of 1992’s Bram Stoker’s Dracula. “In that scene, Francis [Ford Coppola] used a real Romanian priest,” she explained to Entertainment Weekly in 2018. “We shot the master and he did the whole thing. So I think we’re married.”

Credit: Shutterstock (2)

China Chow

Reeves was first linked to his former flame, who is the daughter of restaurateur Michael Chow, in June 2008 when they were seen in the Mediterranean Sea together. The actor never confirmed the fling, but they parted ways shortly after their French Riviera vacation. The duo reunited at the Geffen Contemporary at Museum of Contemporary Art in May 2019, and an onlooker told Us that China was “hitting on Keanu hardcore.”

Credit: Shutterstock

Sandra Bullock

No, the Lake House costars never dated but both parties admitted to having a crush on each other while working together on Speed in the mid-‘90s. During his debut appearance on The Ellen DeGeneres Show, Reeves watched an old clip of Bullock confessing her secret crush on the actor when she joined the daytime show a while back. The My Own Private Idaho star, for his part, revealed that the feelings were mutual. “She obviously didn’t know I had a crush on her,” he said.

Credit: Matt Baron/Shutterstock

Alexandra Grant

Reeves made headlines when he stepped out with Grant at the LACMA Art + Film Gala in November 2019, as the longtime friends hit the event’s red carpet hand in hand. Though it’s been a while since fans have seen the Point Break star with a significant other, a source told Us that the duo “have been dating for years.”