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Keanu Reeves has had many memorable kissing scenes with a few onscreen partners. There was one make-out sequence, however, that Reeves remembered for the wrong reasons.

Keanu Reeves on his ‘most painful kiss ever’

Keanu Reeves posing at the 'Toy Story 4' premiere in a suit.
Keanu Reeves | Axelle/Bauer-Griffin/FilmMagic

Many stars have had nothing but praise for Reeves’ onscreen kissing skills. Some, like Diane Keaton, have admitted to even getting flustered by smooching the star. So much so that she felt embarrassed kissing her much younger partner in Something’s Gotta Give.

“It was pretty embarrassing, and for Keanu, too,” Keaton once said according to the Sydney Morning Herald. “It has to do with time of life. It’s instinctive – [while kissing him] you go, ‘Uh, probably not!’ And Keanu was going, ‘Definitely not!’ He was trying to be polite. But he’s so beautiful, it’s stupefying. It was a guilty pleasure. A very guilty pleasure.”

Reeves has often had similar kind words for his co-stars. But there was one kissing scene in his career he didn’t find ideal. In 1995, Reeves starred in the period drama A Walk in the Clouds. There, he falls for a character played by Spanish actor Aitana Sanchez-Gijon.

The day before kissing Sanchez-Gijon, Reeves was injured in a sporting accident that required him to receive four stitches in his mouth. He still had to kiss Sanchez-Gijon the next day, which made for an uncomfortable experience. But Reeves asserted his own physical discomfort might have been good for the movie.

“Yeah, it was the most painful kiss ever,” he once told The Virginia Pilot. “But maybe that helped the scene. Aitana was very sweet. She knew I was suffering, but I had to do it.”

Carrie-Anne Moss once called her ‘Matrix Reloaded’ kiss with Keanu Reeves ‘erotic’

Moss was another familiar co-star who was intimate with Reeves on many occasions for The Matrix films. In the second movie of the franchise Reloaded, the two filmed an even steamier scene together than in the first movie. Moss admitted she felt slightly anxious about the upcoming moment, but Reeves was there to ease her worries.

“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,” Moss once said in an interview with The Morning Call.

But what made the scene in question stand out for Moss was the makeup. In the Matrix movies, some human beings outside in the real world have outlets attached to their bodies. These outlets are used to plug characters into the virtual reality of The Matrix. And they’re also what added a little extra level of intimacy to Moss’ and Reeves’ love scene.

“What was weird was that we had hours of applying those plugs on our backs before we would shoot every day. And, in a way, it’s kind of erotic because you’re like, ‘What is that? What did I just see?’ You’re not seeing any body parts, but you’re seeing these plugs,” she said.

Keanu Reeves’ other ‘Matrix’ co-star said she kissed him every 8 years

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Moss wasn’t the only actor in The Matrix franchise who Reeves had an intimate scene with. In Reloaded, Reeves also locked lips with actor Monica Belluci, who had a supporting role as Persephone. Belluci’s shared that her kiss with Reeves was the opposite of painful. But she was also very familiar with kissing her co-star in previous films.

“It took us two days to shoot a single kissing scene,” Belluci recalled. “We did the scene with very many clothes, then less clothes, then less clothes, and we had to do the scene maybe 50 times. Keanu is a good kisser, so it wasn’t painful. Nine years ago, when I did Bram Stoker’s Dracula and I was just a model, I had to kiss Keanu in that. Every eight years, I kiss Keanu Reeves.”