Kate Hudson and Matthew McConaughey Reunite for 'How to Lose a Guy in 10 Days' 20th Anniversary

The co-stars shared memories about working on the film and revealed where they think their characters are now.

Kate Hudson and Matthew McConaughey reunited to celebrate the 20th anniversary of How to Lose a Guy in 10 Days, which first debuted in theaters on Feb. 7, 2003. The two stars appeared on Instagram Live to discuss their hit rom-com, revisit memories of working together and imagine where their characters are now. 

"It's crazy," Hudson said as she kicked off the live chat between her and her co-star. 

She then told McConaughey about how the film has found a new audience thanks to it becoming a viral sensation on TikTok, with young fans now coming up to her to discuss it. "Thee's been this whole, like, viral TikTok, How to Lose a Guy moment and [it's] basically introduced our movie to an entirely new generation of young kids," she said.   

"They're in on the joke," McConaughey said of how people watch the film now, appreciating "the mischievous fun" going on between their two characters. 

In the movie, which was adapted from a book by Michele Alexander and Jeannie Long, Hudson plays a women's magazine writer, Andie Anderson, who is writing an article about how to get a man to dump her. McConaughey, meanwhile, plays an advertising executive named Benjamin Barry, who makes a bet that he can make any woman fall in love with him. After a chance meeting, the two embark on their quests only to fall for each after breaking each other's hearts. 

Hudson then shared some of the fans' questions about the film before both of them answered. 

"It's professional. Like, we're actually trying to create something that evokes something in a certain way that might not exactly be the way you would necessarily do it in real life," Hudson, 43, said of what it's like to film a kissing scene, which is something she's always asked about when it comes to How to Lose a Guy in 10 Days, before revealing, "We do kiss nicely." 

"I would have to agree with you," McConaughey added. 

As for who came up with the nickname, Benny Boo Boo? Well, that was likely Hudson at the moment. "I can't remember if that was something written or if it just came out of my mouth," she said while McConaughey asserted that it was likely her and not something written in the script. 

McConaughey then revealed that after the moment Andie calls Ben that, he would break up in laughter. "That was one of my bigger laughs. I loved seeing Ben squirm," he shared. 

McConaughey then brought up the movie's poster, which features the two co-stars leaning against each other. It's a pose that's been recreated by many rom-coms that followed, including "ones that I've been in," the 53-year-old actor joked. Hudson said it was they who figured out the lean, but she's not sure if she was actually in the yellow dress or if it was photoshopped onto her after the fact. 

Hudson then reflected on how iconic that dress has become, noting "the color, the simplicity of it" is what made it so memorable. "It's crazy that the yellow dress has lived on," she said, before revealing that "a woman wrote in that she got married in it."

Later, the two discussed filming the "You're So Vain" singing moment that happens near the end at the gala. "We made it work," Hudson said of "that big moment, the big set piece." 

She added, "I think that's what made the film work so much… The comedy allowed itself to go really far without being broad. It allowed for us to go further." McConaughey then responded by saying sometimes "you go too far," but here they were able to "push it really hard" and not lose the audience. 

When it came to the chemistry seen between the two, "we were two heavyweights going at it," McConaughey said of him and Hudson working together in the film. "We enjoyed going toe-to-toe… We knew it wasn't personal." 

"We're tough-skinned," Hudson added, calling back to the mischievous, combative element that played out between Andie and Ben. She added, "We're both very free… There's something spontaneous about the way we were able to work together." 

As for where Andie and Ben are now, "I hope they're still happy and like adventures and doing what they wanna be doing and have kids and made it work," Hudson said of her dream or "real version" for them. However, if this was another movie, Hudson has to imagine there's "conflict" between them in order for there to be a reason to revisit the couple. 

Leading up to the anniversary, both Hudson and McConaughey took part in an oral history with Vanity Fair, recounting even more memories from behind the scenes. That led McConaughey to reveal that a fortune teller convinced him to join the project. 

"I remember considering whether I was going to do it or not one night while on a walk down Sunset Boulevard when suddenly, this guy comes up out of nowhere to me -- he was a fortune teller guru [and] goes, 'Can I tell you your fortune real quick?'" the actor recalled. 

"I was like, 'Yeah, man. Sure.' He immediately goes, 'There’s a movie you’re considering right now. It’s a romantic comedy. You have to do this or it will be one of the biggest regrets of your life. It is going to be a blast, it is going to be an incredible experience and it is going to make a bunch of money,''" he continued, revealing that the moment gave him pause before ultimately accepting. 

McConaughey concluded, "I remember thinking, Did the studio hire this guy? I laughed at the thought, but I also remember taking a more serious consideration. I think I even accepted the offer the next day."