Keanu Reeves has been single for so long that it was a very big deal how he stepped out with new GF Alexandra Grant. She’s the first woman he’s brought as date on a red carpet.

Keanu Reeves has long been one of the most eligible bachelors in Hollywood. But despite his handsome looks and kind demeanor, he hasn’t had a public girlfriend in nearly 20 years. Which makes his new squeeze Alexandra Grant a VERY big deal. The 55-year-old John Wick star held hands with the 46-year-old artist as they posed on the red carpet of the LACMA Art + Film Gala Presented By Gucci in Los Angeles on Nov. 2. She was also photographed looking adoringly at the actor, and they never stopped touching while posing.

Not only is it huge news that Keanu has a girlfriend, never in his 35 year Hollywood career has he brought a love interest as a date to a red carpet. The pair has actually known each other for quite some time as Alexandra illustrated Keanu’s 2011 adult’s picture book, Ode to Happiness to which he provided the text, of which Google books described as “a charming reminder not to take oneself too seriously.” The pair also collaborated on the 2016 book Shadows.

The two have posed together on a red carpet before, but not as a romantic couple. They stood by each other at the UNAIDS Gala during Art Basel 2016 in Basel, Switzerland on June 13, 2016. But there was no hand-holding and looks of adoration like there was at the LACMA event. The pair’s professional relationship continued in 2017 as they started a publishing company together and travelled to Paris to promote Ode to Happiness, posing together at book shops.

In 2018, Alexandra opened up about her business partnership with Keanu, telling Los Angeles Magazine “We really like [a] ‘can-do’ [attitude,]. Some people are kind of dreamers who have a lot of ideas but don’t like to get things done. I think we both like to have the idea and get it into the world.” It looks like their professional commitment to each other has blossomed into romance.

Keanu’s last known public girlfriend was aspiring actress Jennifer Syme. She gave birth to their daughter Ava Archer Syme-Reeves while eight months pregnant on Dec. 1999 but the infant was stillborn. Following the heartbreak, the pair split up but remained friends. Tragedy would follow again, as Jennifer died in a car accident on April 2, 2001 when she crashed her Jeep Cherokee into a row of parked cars in Hollywood while trying to return to a party at Marilyn Manson‘s house. She’s buried next to her daughter with Keanu in a Westwood, CA cemetery.