In an Instagram live on Monday, Hudson and McConaughey reunited to talk about the romantic comedy and how it continues to be a classic film.
"I think it's so amazing," Hudson said. "We got lucky to be in such a classic one you know."
"I always ask what it is and I know when I've been with people watching it, there's sort of a mischievous fun they're having," McConaughey said. "It's sort of an interactive experience they're having."
The film follows Hudson's character, Andie Anderson, as a magazine columnist who devised a plan to dupe a man, Ben Berry, played by McConaughey, into leaving her in 10 days.
Like all good rom-coms, the two end up falling for each other in the end.
The two discussed favorite lines in the film; Andie's iconic yellow dress; Carly Simon's "You're so Vain," which was sung on two different occasions in the film; the iconic movie poster; and memorable moments from being on set, including the on-screen kisses that audiences loved, but were hard to film.
"Everyone wants to know ... what's it like to kiss McConaughey," Hudson began. "And my whole thing is we're always in weird environments. There was only one time when we kissed that was so nice and gentle in the bathroom."
"Yeah, everything else was not climate control," McConughey added.
"Or you're on the Brooklyn Bridge and the wind is blowing in your face. It's so true," Hudson said.
Hudson, who said that she always gets asked about her and McConaughey's chemistry on "How to Lose a Guy in 10 Days," asked McConaughey how he felt about their chemistry.
"We're two heavyweights going at it -- what I mean by that is, what tickles me, doesn't bruise you. What tickles you, doesn't bruise me," McConaughey said. "We enjoyed going toe to toe. It was fair game and we knew it wasn't personal -- and hopefully the camera's rolling while it's happening."
"We don't take things personally and we are tough-skinned," Hudson said.
"I think we can extend the sense of humor and take the joke further ... We were never afraid to push it where some would consider it to be too far," McConaughey said.
The two also weighed in on what their characters would be up to today. Hudson said she hopes Andie and Ben are happy and have kids, while McConaughey suggested maybe they'd be on their honeymoon in a world where a sequel was made.
Since the film's release in 2003, "How to Lose a Guy in 10 Days" has had a revival on social media with many dueting some of the film's lines on TikTok or singing to "You're so Vain."
"There's been this whole viral 'How to Lose a Guy' moment and it's basically introduced our movie to an entirely new generation of young kids," Hudson said. "And all these younger kids are re-doing it or lip syncing and doing moments for it."
"I have noticed now that you bring it up," McConaughey told Hudson. "A younger genreation comes up and they're like, we just watched your movie for the fifth time -- and it's very current to them."
In August 2019, it was announced that a new version of "How to Lose a Guy in 10 Days" was being adapted into a television series for Quibi. However, the streaming platform dissolved by December 2020 and no show materialized.