Nostalgia

Keanu Reeves’ Best Onscreen Romances: Winona Ryder, Diane Keaton and More

September 2, 2021

Turning up the heat! From Winona Ryder to Diane Keaton, Keanu Reeves has been making his leading ladies swoon for decades.

The Canadian actor first teamed up with Ryder for 1992’s Bram Stoker’s Dracula and the duo later reunited for 2006’s A Scanner Darkly. More than a decade later, the pair took on roles in 2018’s Destination Wedding, a quirky romantic comedy that sees their characters move from enemies to lovers as they connect over their shared hatred of weddings.

“I wish I could do every movie with him,” the Stranger Things actress told Entertainment Weekly in August 2018. “The biggest thing for me was the opportunity to get to work with Keanu again. It was a very surprising script in that it doesn’t really have the tropes that a lot of romantic comedies do. … It’s refreshing and sort of a challenge. It was a special time. Any time with Keanu is a special time for me.”

Reeves, for his part, couldn’t imagine making the film without Ryder by his side. “Having known each other for so long, with that is also the rapport, the trust. We have a mutual outlook on the world. In terms of working together, we’re cut from the same cloth,” he told the outlet. “There is that trust; there is that facility. … We know each other, we love each other, we’re fans of each other’s.”

Fans of romantic comedies know Reeves has a knack for playing up his more charismatic side, as portrayed in 2003’s Something’s Gotta Give. Though his character may not have ended up with Keaton’s in the Nancy Meyers classic, the former costars reminded viewers of their undeniable chemistry while reuniting at the 2020 Oscars.

“It’s been a long time since you and I made that movie. Remember Something’s Gotta Give?” Keaton teased before the pair announced the winner for Best Original Screenplay. “That was a lot of crying in there, Keanu, lots of laughing and crying. And well, we had some really, well let’s be frank, good times.”

While Reeves teased that the best times on that movie’s set were between Keaton and Jack Nicholson — whose character famously gets the girl — Meyers was as pleased by the reunion as her biggest fans.

“Whoa,” she teased via Instagram at the time. “Maybe they did end up together.”

Scroll down to relive more of Reeves’ best onscreen romances!

Credit: YouTube; Shutterstock (3)

Keanu Reeves' Best Onscreen Romances: Winona Ryder, Diane Keaton and More

Turning up the heat! From Winona Ryder to Diane Keaton, Keanu Reeves has been making his leading ladies swoon for decades. The Canadian actor first teamed up with Ryder for 1992's Bram Stoker’s Dracula and the duo later reunited for 2006's A Scanner Darkly. More than a decade later, the pair took on roles in 2018's Destination Wedding, a quirky romantic comedy that sees their characters move from enemies to lovers as they connect over their shared hatred of weddings. "I wish I could do every movie with him," the Stranger Things actress told Entertainment Weekly in August 2018. "The biggest thing for me was the opportunity to get to work with Keanu again. It was a very surprising script in that it doesn’t really have the tropes that a lot of romantic comedies do. ... It’s refreshing and sort of a challenge. It was a special time. Any time with Keanu is a special time for me." Reeves, for his part, couldn't imagine making the film without Ryder by his side. "Having known each other for so long, with that is also the rapport, the trust. We have a mutual outlook on the world. In terms of working together, we’re cut from the same cloth," he told the outlet. "There is that trust; there is that facility. ... We know each other, we love each other, we're fans of each other's." [jwplayer tCcvpqs0] Fans of romantic comedies know Reeves has a knack for playing up his more charismatic side, as portrayed in 2003's Something's Gotta Give. Though his character may not have ended up with Keaton's in the Nancy Meyers classic, the former costars reminded viewers of their undeniable chemistry while reuniting at the 2020 Oscars. "It's been a long time since you and I made that movie. Remember Something's Gotta Give?" Keaton teased before the pair announced the winner for Best Original Screenplay. "That was a lot of crying in there, Keanu, lots of laughing and crying. And well, we had some really, well let's be frank, good times." While Reeves teased that the best times on that movie's set were between Keaton and Jack Nicholson — whose character famously gets the girl — Meyers was as pleased by the reunion as her biggest fans. "Whoa," she teased via Instagram at the time. "Maybe they did end up together." Scroll down to relive more of Reeves' best onscreen romances! [podcast_block]

Credit: Moviestore/Shutterstock

'Tune in Tomorrow' (1990)

Based on the novel Aunt Julia and the Scriptwriter, Reeves stars as radio station employee Martin Loader who falls for his Aunt Julia (Barbara Hershey). While the duo isn't related by blood, a scriptwriter catches wind of their "scandalous" affair and the pair later find themselves to be the subject of a new radio drama.

Credit: Merie W Wallace/Warner Bros/Kobal/Shutterstock

'Sweet November' (2001)

Workaholic Nelson Moss (Reeves) meets free spirited Sara Deever (Charlize Theron) and the pair fall in love after spending the entire month of November together. Their relationship hits hard times when Sara reveals that she's been diagnosed with a terminal form of cancer. Though Nelson vows to love Sara no matter what, she asks him to leave so that he'll only have happy memories of their time together.

Credit: Moviestore/Shutterstock

'Something's Gotta Give' (2003)

A fan-favorite, this Meyers classic casts Reeves as a doctor who is swept off of his feet by divorced playwright Erica Barry (Keaton). Though the couple doesn't end up together at the end of the film, the performance is widely referred to as Reeves' best romantic role.

Credit: over usage. Mandatory Credit: Photo by Peter Sorel/Warner Bros/Village Roadshow/Kobal/Shutterstock

'The Lake House' (2006)

More than a decade after working together in 1994's Speed, Reeves and Sandra Bullock teamed up once more for a heartbreaking romantic drama. Dr. Kate Forster (Bullock) leaves a note for the next tenant of a rented lake house in Wisconsin. Alex Wyler (Reeves) discovers her message two years later and the pair continued to write to one another, hoping to finally meet one day and earn their happily ever after.

Credit: Evevation Filmworks/Kobal/Shutterstock

'The Private Lives of Pippa Lee' (2009)

After a rough upbringing, Pippa (Robin Wright) marries a man 30 years her senior and settles down. Though she spent much of her marriage aiming to be the perfect wife, she sparks an affair with a younger man (Reeves) after her husband cheated with one of her closest friends.

Credit: YouTube

'Destination Wedding' (2018)

Ryder and Reeves begin this quirky comedy as strangers attending the same wedding but eventually realize they have a lot in common. The duo vows to stick together throughout the event — and sparks start to fly.

Credit: Doane Gregory/Netflix/Kobal/Shutterstock

'Always Be My Maybe' (2019)

This Netflix original movie gave Reeves' career a renaissance — and proved that he still has impeccable comedic timing. Starring as himself, Reeves wins over celebrity chef Sasha Tran (Ali Wong) before she finally realizes her childhood best friend (Randall Park) is her perfect match.

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