Keanu Reeves' history of red carpet dates seems less than romantic at first glance. But he finally broke his streak of stag appearances in 2019 when he walked hand-in-hand with his girlfriend Alexandra Grant. But who else has he graced the red carpet with? Let's find out!

Reeves has endured some tragedies in his life, including a stillborn child and the death of his former girlfriend Jennifer Syme in a car accident. In 2006, he told Parade Magazine,

"Grief changes shape, but it never ends. People have a misconception that you can deal with it and say, 'It's gone, and I'm better.' They're wrong. When the people you love are gone, you're alone."

Thankfully, it looks like Reeves isn't alone anymore. In 2019, he debuted his relationship with artist Alexandra Grant at the LACMA Art + Film Gala red carpet. According to InStyle, this was the first time Reeves ever brought an official romantic date as his plus-one, even if the tabloids would argue that some of the co-stars he's appeared with should count. After all, it's often tough to tell when celebs are walking the line between colleague and secret romance.

As for Reeves and Grant, they've been creative partners for a long time, and it's unclear exactly when their relationship made the jump into romance. She collaborated with him on his books Ode to Happiness and Shadows, and they also founded a publishing house together in 2017 called X Artists' Books. Keep watching to learn The Truth Behind All Of Keanu Reeves' Red Carpet Dates!

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Alexandra Grant | 0:00

Rachel Weisz | 1:21

Kim Reeves and Karina Miller | 2:14

Brenda Davis | 2:32

Charlize Theron | 4:27

Carrie-Anne Moss | 5:30

Sandra Bullock | 6:25

Tiger Hu Chen | 7:33

Winona Ryder | 8:14

Halle Berry | 9:24

Patricia Taylor | 10:18