A Timeline Of Every Keanu Reeves Red Carpet Date

We're right in the middle of the Keanaissance. As of this writing, the star is already shooting The Matrix 4, extinguishing any hopes that tiny sunglasses will fall out of fashion sometime soon; Toy Story 4 is now an Oscar winner; and we're still reeling from his epic self-parody in Netflix's Always Be My Maybe. Keanu Reeves is indeed the Internet's Boyfriend — and our boyfriends in the daydreams we have where he slides into our DMs. Nonetheless, Hollywood's No. 1 nice guy rarely appears to be actually dating anyone.

Reeves is notoriously private about his love life and rarely shows up on the red carpet with a date who he's actually dating, if he even brings a date at all. This made his shocking 2019 appearance with girlfriend Alexandra Grant even more headline-worthy. Could Keanu finally be Naruto-running towards love?

From his co-stars to his sisters, Reeves history of red carpet dates seems anything but romantic — at least on the record.

Keanu Reeves isn't the lonely guy anymore

That now-famous Keanu Reeves interview where the actor allegedly admitted he was a "lonely guy" may have been a sham, but that doesn't mean we weren't concerned anyway. The star has endured a string of tragedies, including his child's stillbirth and the tragic 2001 death of his former girlfriend Jennifer Syme. "Grief changes shape, but it never ends," he told Parade (via People) in 2006. "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, the star debuted his relationship with artist Alexandra Grant at the LACMA Art + Film Gala red carpet (above). 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 Sandra Bullock, Halle Berry, and Charlize Theron should totally count. After all, it's often tough to tell when celebs are walking the line between colleague and secret romance. But we'll get to those, as well as the rest of Reeves' eclectic red carpet dates momentarily. 

We do know that Reeves and Grant have been creative partners for a long time, and it's unclear when their relationship crossed the line into romance. According to People, she worked on his books Ode to Happiness (2011) and Shadows (2016). They also founded a publishing house in 2017 called X Artists' Books.

When Keanu Reeves was Rachel Weisz' plus one

Keanu Reeves and Rachel Weisz played on-screen love interests in the 1996 flick Chain Reaction, which triggered rumors of an off-screen romance. Do you blame the tabloids? According to PopSugar, Weisz took Reeves to the premiere of her movie Stealing Beauty, which he was not at all involved in. How many of us actually take our colleagues to really important life events? How many colleagues would attend said event if they were hobbling around on crutches? Reeves had just broken his ankle in a motorcycle accident.

Nonetheless, Weisz — who has appeared on numerous red carpets with the star — has been adamant about their platonic relationship. Though, she did appreciate the gifts fans gave her to pass along to The Matrix lead.

"A love affair with Keanu? No way," she told Women's Own (via Whoa Is Not Me) in 1996. "We were chasing round all over the place, trying to save our skins. It was very intense but there was no time for anything like that ... Actually, it was amazing. Girls would hand me baskets of fruit to give to him and I had to say: 'I'm not seeing him... I can't just turn up at his house.'"

Sister Act I

Hard times can bring a family closer or it can tear them apart. For Keanu Reeves and his only biological sister Kim Reeves (above left), the hardship of a cancer diagnosis helped the pair foster an unbreakable bond. In 1991, Kim was pursuing a career in Hollywood when she was diagnosed with leukemia at the age of 25. Though Keanu had four movies coming out that year, he rarely left her side throughout the difficult course of treatment. "When she was in the hospital, he was there with her all the time, sitting at her bedside, holding her hand," an insider told People (via MSN).

In 1995, a handful of years before Kim went into remission, it seemed like the pair was closer than ever. According to a profile in People, Keanu didn't have a home at the time. Between filming, he'd either rent a hotel room or crash with his sister. They liked to ride horses, cook dinner, and watch VHS tapes (remember those?). "My brother is my prince," she gushed to the magazine. "He listens to every word, to every comma after every word, that you are saying."

Kim eventually went into remission in 1999, the same year she accompanied her brother to the premiere of The Matrix (above). According to MSN, the actor reportedly donated 70 percent of his Matrix earnings "to hospitals that treat leukemia."

High school friends in highest places

Keanu Reeves really seems like the kind of guy who nurtures his oldest relationships despite the fact that he's totally famous now. It's unlikely that he'd ever force someone he cared about into an Uber Pool like the obnoxious parody of himself that he played in Always Be My Maybe. Proof? The guy still reps his high school friends hard.

In 2000, Reeves took his old high school bestie Brenda Davis to the Oscars. Talk about having friends in high places. At this time, Reeves was at the height of his Matrix fame and awaiting the release of The Replacements. The pair also hit up Vanity Fair's post Oscars bash, which they're pictured at above.

According to the Orlando Sentinel, Davis helped Reeves through a number of hardships, including his sister's cancer diagnosis and his first child's stillbirth. It makes sense that he'd want her by his side for a moment as big as the Academy Awards — and now, they may actually be bona fide family. According to rumors (which are hard to confirm since Reeves is so tight-lipped in the press) Davis named Reeves her daughter's godfather. Just Jared does confirm that his goddaughter is named Isabella, who looks an awful lot like the girl standing next to Davis in a paparazzi shot.

Charlize Theron and Keanu Reeves sure look like a couple

It's impossible to tell if Charlize Theron and Keanu Reeves actually dated since they hit up the red carpet as co-stars, but it's hard to say that they didn't date. Things get muddied up when you start playing lovers on-screen. It all started back in 2001 when Theron and Reeves showed undeniable chemistry in the emotional drama Sweet November. That year, they embraced each other on the Golden Globes red carpet (pictured right) and were spotted getting cozy at Style Magazine's after party. The kicker? Charlize brought along her mom, who held Reeves' hand. Cue the relationship rumors!

And those romance rumors have somehow managed to span across a decade. According to the Daily Mail, the pair was spotted "getting touchy-feely" after leaving a Beverly Hills restaurant in 2010 (yes, this reportedly included "a series of kisses and hugs"). They allegedly backed off as soon as they realized they had been caught by the paps. At the time, Theron had just gotten out of a nine-year relationship, but that didn't stop her and Reeves from "constantly laughing, almost disrupting other tables with how loud they were" and being "wrapped up in each other's conversation and having a great time together." We'll probably never really know what was up. Reeves is a master of subtlety.

Once you're in Keanu's Matrix, you're in for good

Keanu Reeves and Carrie-Anne Moss have certainly gotten close over the years. They are, after all, team up to save humanity from enslavement at the hands of malicious AI. Plus, not too many people have been kicking it with the same co-stars for two decades, unless you're a regular on Law & Order: SVU. As a result, it's not uncommon to see them together on the red carpet.

Though Reeves typically flies solo, he did escort a pregnant Moss on the red carpet while promoting The Matrix Reloaded at Cannes Film Festival in 2003. Honestly, do we expect anything less than a gentleman from the guy who regularly uses the hover hand to avoid touching women while posing for photos. It doesn't get much more respectful than that.

Moss and Reeves have an undoubtedly supportive relationship, the kind that can endure an awkward love scene or two. In an interview with The Morning Call, the actress admitted that Reeves helped ease her nerves before they got intimate for the cameras while shooting The Matrix Reloaded. "I was pretty nervous about the love scene but, in the end, Keanu's a good friend of mine and I trust him. I respect him. I like him," she said.

Is Sandra Bullock the one that got away?

Sandra Bullock and Keanu Reeves may always be each others' one that got away. The pair — who attended the 2006 Academy Awards together (pictured above) — had mutual crushes, but never once took their relationship to the next level. In fact, that's why Bullock believes they've been able to maintain such a solid friendship.

Both Bullock and Reeves starred in 1994's Speed, and Bullock — who's first big break was the film — immediately found it hard to concentrate around him. In an interview with Ellen DeGeneres, she admitted, "I think about how sweet Keanu Reeves was and how handsome he was. It was hard for me to really be serious ... Never dated him. There was just something about me that I guess he just didn't like." Except, Reeves did like her.

When Reeves sat down with DeGeneres months later, the actor admitted that he had no idea Bullock was crushing. "She obviously didn't know I had a crush on her either," he said, using work as an excuse as to why things never escalated. A professional king, but it's never too late to shoot your shot!

A director and his muse

Keanu Reeves kept up his tradition of taking non-romantic dates to red carpets when he appeared at the Toronto International Film Festival with Matrix stutman Tiger Hu Chen in 2013. Judging by the photos, the pair was inseparable. Sometimes, you just have to support your bros.

Reeves and Chen were at TIFF to promote their film Man of Tai Chi. According to The Star, the flick was Reeves' directorial debut, and he was specifically inspired by Chen, who trained him throughout The Matrix. In fact, the whole film was created for Chen. "We wanted to work together, so over the years we came up with a story about the traditional aspect of Tiger — he's a (martial arts) master — but he's also a modern guy," Reeves told The Star. "He grew up in Chengdu, moved to Beijing and became a big stuntman. So the story was born out of that."

Overall, the film received decent ratings from critics. As of this writing, it remains Reeves' only credited project as director, though he's produced a number of films since. Never underestimate the true creative power of friendship.

Now introducing, Mr. and Mrs. Keanu Reeves

Throughout Keanu Reeves and Winona Ryder's decades-long friendship, the pair has gotten walking the red carpet together down to a science. The pair starred in 2006's A Scanner Darkly and 2009's The Private Lives of Pippa Lee, but they first crossed paths in 1992 while working A Bram Stoker's Dracula. While Alexandra Grant remains Reeves' only red carpet date that he's, well, actually confirmed to be dating, Ryder is his only date that he's actually married to. Yes, in the bizarre fever dream that was 2018, Ryder actually admitted that the two '90s icons accidentally got married while filming Dracula.

"I swear to god I think we're married in real life." she told Entertainment Weekly. "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."

As far as an actual romance, not so much, but they did reunite for a second round of nuptials in 2018's Destination Wedding. This time, they were only guests. Next up: Divorce Story. Oh wait, that's Adam Driver. Sorry — must be the hair.

Sister Act 2

Though Keanu Reeves is the master of a solo red carpet walk, he is certainly not above being someone else's plus one. The star is supremely supportive of his half-sister Karina Miller, who shares the same mom. It doesn't seem like there's any sibling rivalry.

One of the first times we saw Miller was alongside her brother at the premiere of The Matrix. Twenty years later, the tables turned when Keanu accompanied her to the premiere of her Lionsgate flick, Semper Pi. According to the Daily Mail, Miller produced the action film which starred Leighton Meester and Jai Courtney. At the premiere, Reeves seemed to push the spotlight off The Matrix 4 and towards his sister's project. "It's really awesome to be here and be invited," he told Entertainment Tonight. "It's a great accomplishment, it's a wonderful film."

Similarly, Miller gushed about her older brother. "He's always been so supportive and so protective of me doing my own thing," she told Entertainment Tonight. "I always really appreciate that so. And it was fun to have family here because our mom is out of town still." While mama's away, the kids will apparently play very nice.

Keanu Reeves was all smiles with Halle Berry

Rumors of a steamy romance between Keanu Reeves and his John Wick: Chapter 3 – Parabellum co-star Halle Berry ignited in 2019 during the press cycle for the film, where they were spotted smiling on red carpets and events across the country despite never officially being each other's plus one. You don't need to be a plus one if you're already invited, right?

These rumors — albeit fun to think about — are undeniably thin. Someone apparently told Life & Style (via HollywoodLife) that even before they picked up with John Wick: Chapter 3, "they started getting to know each other" and "realized there was something there that was stronger than friendship." Apparently, Reeves is "totally" Berry's type, though we'd argue that there's nary a soul who wouldn't date Hollywood's reigning nice guy.

Gossip Cop got hold of an apparent Berry source who shut down the rumors. Enduring the lengthy press tour for the blockbuster action flick probably just made Reeves and his co-star very comfortable with each other. Besides, he looks pretty smitten with Alexandra Grant.

Keanu Reeves is a total mama's boy and we love it

If we needed anymore evidence that Keanu Reeves is the type of guy you'd want to bring home to your mama, it's this: the star brought his own mother, costume designer Patricia Taylor, as his date for the 2020 Academy Awards. Who doesn't love a mama's boy?

This isn't the first time Reeves has brought his mom along for the ride, though the Oscars were a particularly big day for the pair. Reeves lent his voice to Toy Story 4, which ended up winning in the best animated feature category. Taylor even did a great job with the red carpet interviews and totally zipped her lips when Ryan Seacrest asked her to dish on The Matrix 4. A good mom knows how to keep a secret, only some fans didn't get the memo that this was, indeed, Reeves' mother.

As the Huffington Post awarded the John Wick star with the title of "Best Son" (an arguably more important win than some Hollywood award) some viewers apparently mistook Taylor for Reeves' girlfriend. Never mind the fact that Grant and Taylor have about 30 years between them (though this could be a testament to the fact that his mom looked absolutely stunning in her pants suit). According to the Independent, even Getty Images misidentified Taylor in a caption. Get it together, guys! Not all women with gray hair are the same.