‘How to Lose a Guy in 10 Days’ Turns 20! See Photos of the Cast Then and Now

Our … family … album! It’s hard to believe How to Lose a Guy in 10 Days turned 20 years old in February 2023, but what’s harder to believe is that the cast of the beloved romantic comedy has barely aged since then. 

Starring Kate Hudson and Matthew McConaughey – with Kathryn Hahn, Annie Parisse, Adam Goldberg and Thomas Lennon lending their comedic acting chops in supporting roles – How to Lose a Guy in 10 Days has remained as popular as the day it hit theaters two decades ago. 

“I’ve always thought about what Matthew and I’s characters would be now, if we were still together,” Kate, who portrayed the lovable, go-getter journalist Andie Anderson in the hit film, recalled to Elle magazine in August 2020. “It’s actually probably a good amount of time [that has passed] to make a movie about it. We probably would have gotten married with kids. We’re probably miserable right now!”

Though the Almost Famous star revealed that she didn’t have high hopes for where she and the True Detective actor’s characters would be in their relationship, Kate told the outlet that Andie would be thriving in her career.  

“I think Andie Anderson is ambitious, and she was wanting to go places, and she was sort of stuck in this job,” the mom of three explained. “I loved what we created with that movie. And she found love that would support her ambitions. Andie would probably be running something at this point.”

While speaking with Entertainment Weekly in February 2018, Kathryn – who reunited with Kate on screen in Netflix’s Knives Out: A Glass Onion Mystery in September 2022 – opened up about working with the Bride Wars star and the rest of the star-studded cast as her career began to take off in the early 2000s.

“It felt like such a big budget movie to me,” she told the outlet. “Kate Hudson is a goddess and her star was crazy on the rise — I couldn’t believe I was getting to work with her. Shalom Harlow was this gorgeous model who would come into the hair studio I was working at in L.A., so the first time I met her I was like, ‘Oh, I totally took your coat once.’ She was kind enough to pretend to remember me.”

While reflecting on the film days before its 20-year anniversary, Matthew revealed to Vanity Fair that he almost turned down the role of Benjamin Barry; however, he signed onto the movie after a chance encounter with a fortune teller while walking down Sunset Boulevard in Los Angeles.

“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,’” the Academy Award-winning actor recalled. “I laughed at the thought, but I also remember taking a more serious consideration. I think I even accepted the offer the next day.” 

Keep scrolling to see photos of the cast of How to Lose a Guy in 10 Days then and now!