The Cast of 'How to Lose a Guy in 10 Days,' Then and Now

12:58 PM 2/7/2018

by Deirdre Durkan

From Kate Hudson to Matthew McConaughey, the stars of the blockbuster romantic comedy have had successful careers in film and television.

Fifteen years ago, Kate Hudson and Matthew McConaughey stole audiences' — and each other's — hearts in the movie How to Lose a Guy in 10 Days.

The film, which debuted in what might be called the golden age of rom-coms, starred Hudson as a journalist for Composure magazine who writes the "How to" column. She sets out to prove to her friends that she can make him dump her within 10 days. While she attempts to drive advertising executive Benjamin Barry (McConaughey) away with unique techniques like buying him a “love fern,” pretending she’s a vegetarian and filling his apartment with stuffed animals, she's unaware that Ben has made a bet with his co-workers that he can make her fall in love with him.

The film was released on Feb. 7, 2003, and grossed $161.1 million at the domestic box office (adjusted for inflation), according to Box Office Mojo. Read below to see what the main stars have been up to since then.

  • Kate Hudson as Andie Anderson

    Paramount Pictures/Photofest; Venturelli/WireImage

    Before starring in How to Lose a Guy in 10 Days, Kate Hudson won a Golden Globe and was nominated for an Oscar for Almost Famous. She showed off her acting chops and improv skills as journalist Andie Anderson. The star fully embraced her scenes and even came up with the idea to throw the platter of veggies during Ben’s “boys' night” and saying, "You can't watch Meg Ryan for two hours and not be thinking about another girl," when the pair go to see Sleepless in Seattle. Since the film, Hudson has appeared in several other films, including Bride Wars, Raising Helen and A Little Bit of Heaven, as well as guest-starring on Glee.

    Most recently, Hudson released her book Pretty Happy: Healthy Ways to Love Your Body and began a partnership with Fabletics to launch her own line of workout clothes. 

  • Matthew McConaughey as Benjamin Barry

    Paramount Pictures/Photofest; Gary Miller/Getty Images

    In the early to mid-2000s, McConaughey starred in a slew of romantic comedies, including The Wedding Planner and Failure to Launch. His character, Benjamin Barry, is an advertising executive determined to make Composure magazine writer Andie Anderson fall in love with him over a bet he made. While he nonchalantly claims he can make any girl fall for him, he becomes a victim of Andie’s own assignment. In archetypal rom-com fashion, the pair fall in love and he chases her en route to the airport to profess his feelings.

    Now, McConaughey has rebranded himself away from the leading man in a rom-coms to anti-heroes. The star, who won an Oscar for Dallas Buyers Club in 2014, sparking the term McConaughassance, has undergone major physical transformations for the roles he chooses. In preparation to play a man diagnosed with AIDS for Dallas Buyers Club he lost 38 pounds and for Gold he gained 47 pounds. 

  • Kathryn Hahn as Michelle Rueben

    Paramount Pictures/Photofest; Vera Anderson/WireImage

    Kathryn Hahn played Andie’s best friend, Michelle Rueben, who was clueless in relationships. The comedian has acted in a number of other major comedies, like Step Brothers and We're the Millers and Bad Moms has received recognition for her work, including a SAG and an Emmy nomination for the Amazon series Transparent. She recently starred in Amazon's I Love Dick.

  • Adam Goldberg as Tony

    Paramount Pictures/Photofest; Cindy Ord/Getty Images

    Before appearing as on of Ben’s buddies, Adam Goldberg had a memorable role on Friends in a three-episode arc as Chandler’s crazy roommate, Eddie. Since How to Lose a Guy in 10 Days, Goldberg has appeared in several TV series, like Entourage, Taken, Graves and The Jim Gaffigan Show.