An Iconic Hollywood Star Addressed Rumors About Her Involvement With Keanu Reeves

Reeves has had several high-profile girlfriends since rising to fame in the mid-1980s. His first was Jill Schoelen, a fellow actress he met during his early career shooting Babes in Toyland. The pair were together for a few years before Schoelen moved on to another future A-list heartthrob, Brad Pitt.

In 1992 Reeves walked down the aisle with Winona Ryder. Well, kinda. The pair only meant to say “I do” for the cameras while filming Bram Stoker’s Dracula. But Ryder later told magazine 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.”

Following a fling with Coppola’s daughter, Sofia, Reeves entered into a more serious relationship with PA and actress Jennifer Syme. The couple started dating in 1999 and shortly after, they revealed they were parents-to-be. Sadly, after eight months their baby daughter Ava arrived stillborn. And more tragedy was soon to follow. 

Yes, in 2001 Syme lost her life in a fatal car accident. She and Reeves had already been separated for over a year by this point. But the John Wick star was still left devastated by Syme’s passing. He later told Parade magazine, “I miss being a part of their lives and them being part of mine. I wonder what the present would be like if they were here — what we might have done together.”

Rumors about a two-year relationship with yet another actress, Claire Forlani, were flatly denied by Reeves in 2006. The famously private actor managed to keep his love life out of the tabloids over the next decade. But in 2019 news emerged that Reeves was dating Alexandra Grant, an artist with whom he’d previously collaborated on his Ode to Happiness book. 

The couple seemed to confirm that they were indeed an item when they graced the red carpet together at a Los Angeles art gala. Referring to this public appearance a year later Grant told Vogue magazine, “I think every single person I knew called me in the first week of November and that’s fascinating. But the question I’ve been asking in all of this is, ‘What is the opportunity for good?’”

Grant then proved she shared Reeves’ wariness of the press when she was asked about future wedding bells. The artist replied, “Love at every level is deeply important to my identity. How’s that for dodging the question? I do not believe that isolation is the way. There is a period of isolation that I do as a painter, but I deeply value the experience of being in relationships.”

Some were left surprised by Reeves’ new partner, considering she didn’t fit the usual mold. For one thing, Grant isn’t an actress. And for another, as the artist acknowledged herself, she has a distinctive look. Grant said, “I’m a 6’1” woman with white hair. You know, the idea of fitting in… If I wanted to look like Kim Kardashian, I would have to have surgery removing about a foot off my legs.”

While many were happy that Reeves appeared to have found his true love, others were left sad that this put paid to a happily ever after with someone else. Yes, ever since the pair starred together in 1995 action hit Speed, fans have been willing the actor and Sandra Bullock to become an item in real life. Perhaps even more so after they both appeared separately on The Ellen DeGeneres Show.

Bullock was the first to get fans wondering what could have been when she appeared on the daytime chat show in 2018. The actress admitted she found it hard to keep her composure while shooting Speed because of how much she liked her co-star. Bullock described Reeves as “sweet” and “handsome” and revealed she would often get all giggly whenever he looked at her.

When questioned as to why she and Reeves had never got together, Bullock answered, “I guess there was something about me, I guess he didn’t like. I think we’re probably friends for that long because we didn’t [hook up].” But a year later Reeves confirmed that there were lots of things about Bullock he had liked.

That’s right: in 2019 Reeves also found himself on Ellen’s sofa, where the subject of his views on Bullock inevitably came up. The John Wick star admitted, “She obviously didn’t know I had a crush on her either. It was nice to go to work; she’s such a wonderful person and a wonderful actress.”

This might have been the first time that a potential “Keandra” relationship had been touted. But Reeves and Bullock had regularly sung each other’s praises before. While promoting their second movie venture together, 2006’s The Lake House, the latter had told Entertainment Weekly magazine, “I don’t know what it is, but I love being around Keanu. I really do. He is such a good person.”

In return, Reeves had opened up about why they both relished sharing the screen together. He said, “We just do, and I’m glad because I like her tremendously as a person. I always enjoy watching her work. She is funny as all heck, smart as [a] whip… It was great to have some life under our belts since the last time we worked together.”

Of course, like Reeves, Bullock has had quite the eventful love life. Her first celebrity boyfriend came in 1992 when she began dating her Love Potion No.9 co-star Tate Donovan. The pair later got engaged before going their separate ways after three years. Bullock went on to become friends with another ex of Donovan’s, Jennifer Aniston.

Bullock quickly moved on to footballer Troy Aikman but their relationship soon fizzled out. The Miss Congeniality star then spent a year on the dating scene, a period she described to Detour magazine as “the worst experience I ever had.” In 1996 she got together with film technician Don Padilla but after ten months they called it quits. Maybe, by this point, she was regretting not revealing her true feelings to Reeves.

A two-year relationship with her A Time to Kill co-star Matthew McConaughey then followed, a time that she still looks back on fondly. In 2003 the actress told magazine Cosmopolitan, “There’s a great amount of respect and love. I feel very cared for by Matthew. No matter where he is in his life or where I am in mine — he could be married — I know we would stay close.”

Bullock kept her next two-year relationship with musician Bob Schneider on the down-low, revealing to website Cinema.com that she’d learned from past mistakes about making her private life public. Maybe she’d taken a leaf out of Reeves’ book! Even so, her brief romance with Murder by Numbers co-star Ryan Gosling inevitably took up more column inches. The latter told The Times newspaper in 2011 that Bullock was one of the “greatest girlfriends of all time.”

In 2005 Bullock tied the knot with someone a little different from her usual type. The heavily tattooed Monster Garage host and founder of West Coast Choppers Jesse James certainly looked like a bad boy. And within five years of marriage, he’d more than lived up to such a billing.

Yes, in 2010 James was accused by the press of playing away with several other women. The entrepreneur subsequently issued a public apology to Bullock which read, “There is only one person to blame for this whole situation, and that is me. It’s because of my poor judgment that I deserve everything bad that is coming my way.”

James also expressed his hopes that Bullock would be able to forgive him his indiscretions. But the actress, who’d just won an Academy Award for her leading performance in The Blind Side, didn’t waste any time in giving the biker the elbow. Within just three months of the allegations being made, the pair were officially divorced.

After appearing to live the single life for several years, Bullock reportedly got back in the saddle with pin-up Chris Evans. The Proposal star later joked to showbiz source Entertainment Tonight that they’d not only got married but had since divorced, too. And then in 2015 Bullock entered into a relationship with Bryan Randall, a photographer she’d first met at the birthday bash of her son Louis.

Bullock and Randall have made few public appearances together since they first became an item. But seven years on and the pair appear to still be going strong. In fact, rumors about an impending wedding seem to surface every few months, but the couple have so far resisted the temptation to get hitched.

Until Randall makes an honest woman out of Bullock, certain fans will still be holding out hope that she ends up becoming Mrs Reeves. And in a 2021 interview with Esquire magazine, the actress didn’t entirely put this scenario out of the realm of possibility. When asked whether she and her Speed co-star ever hooked up, she replied “Nope,” before surprisingly adding, “But who knows?”

Bullock went on to add, “Keanu’s a guy who, I feel like, is friends with every woman he’s ever dated. I don’t think there’s anyone who has something horrible to say about him. So maybe we could have survived. I don’t know. But we didn’t have to survive anything. We just get to grow up together on parallel roads and tip our hats and meet for a dinner and try to work together.”

Luckily for their respective other halves Randall and Grant, Bullock believes that keeping things platonic with Reeves was the right move. She told Esquire, “And the longer time goes on, the more in awe I am of the human being. Would I have been able to say that if he had dumped me and made me angry? Probably not.”

Bullock then recalled a moment in the wake of Speed’s success which suggested that Reeves would make the perfect boyfriend. The actress had told her co-star that she’d never experienced the joys of truffles and Champagne before. Shortly after, Reeves arrived unannounced at her newly-bought home with such luxuries in tow. In return, Bullock painted his nails the same shade of black as hers.

But Bullock admitted there was one thing that used to drive her crazy about Reeves, and not necessarily in a good way. She told Esquire, “When I first met him, I would spend as much time as I could filling a silence, just to feel comfortable. And the more I jibber-jabbered on, the quieter he would get.”

Bullock went on to explain, “And I thought, I don’t understand what’s happening! He’s looking at me with eyes of confusion. He’s quiet. Did I say something to offend him? And then a day or two later, he would arrive with a note or a little package, saying, ‘I thought about what you said.’ And he would have his response. How many people do you know like that?”

Reeves’ close friendship with the late River Phoenix, and how he coped with the young star’s death, was also discussed by Bullock in the interview. The tragedy had occurred shortly before Speed started shooting. And the actress was left in awe of how much her co-star was in touch with his emotional side.

Bullock said, “I watched how Keanu grieved. And oh, did he grieve for his friend. He’s very private, but he couldn’t hide that. And just to see that a man like that was able to grieve. And I remember thinking, God, if that’s the tip of the iceberg of his depth, and his level of love and care for a friend — that just draws you in.”

Reeves and Bullock may well have missed the boat when it comes to romance. But that doesn’t mean we won’t get to see the longtime friends sharing the big screen again. The latter told Esquire that there’s one particular idea she hopes will come to fruition in the distant future.

Bullock said, “I would love nothing more than to do a comedy with Keanu before we die. Just laugh with him. He’s funny. We can be 75 — it’ll be even better then, like an old-people Cocoon thing. We play two funny old people. A road trip. Just put us in an RV as old people. It’ll be the bookend of Speed! We’ll just be driving really slowly.”

Of course, Reeves famously turned down the opportunity to star alongside Bullock in Speed 2. And the decreasing box-office returns and critical mauling of the 1997 sequel proved he was wise to say, “No thanks.” But why exactly did Reeves pass on the chance to work with one of his closest Hollywood friends again?

Well, it wasn’t anything to do with the actress herself, as Reeves explained in a TV interview on The Graham Norton Show in 2021. He said, “At the time I didn’t respond to the script. I really wanted to work with Sandra Bullock, I loved playing Jack Traven, and I loved Speed, but an ocean liner? I had nothing against the artists involved, but at that time I had the feeling it just wasn’t right.”

Bullock and Reeves shippers will be pleased to know that the latter hasn’t totally ruled out a return to the Speed franchise, though. He told website Movie Web that same year, “You know, I can’t say never. Because I’m standing here for Matrix Resurrections and at the end of the trilogy I did die, so you can’t say never.”

And Bullock isn’t the only actress who has nothing but positive things to say about Reeves. In 2021 the actor appeared on Drew Barrymore’s daytime talk show. And the former child star couldn’t stop gushing about the time she spent filming Babes in Toyland back in 1986 with her special guest.

Barrymore recalled how Reeves made her 16th birthday party particularly special by taking her for a spin on his motorbike around Los Angeles. She said, “And I was so free. I was such a free human being, and it was just this moment where I just remember loving life and being so happy, and I hold it so dear because the older we get, the harder it is to get to that feeling.”

Reeves responded in typically low-key fashion with an “Oh wow,” before adding, “We probably went fast.” Barrymore confirmed that they did indeed go fast, concluding, “We just blasted through the streets. It was at night and the streets were empty, and it was one of those moments where I’ll never forget it.”