How To Lose A Guy In 10 Days is one of the timeless early ’00s romantic-comedies that never gets old no matter how many times you watch it. The film was released on Feb. 7, 2003, instantly captured our hearts. Fans fell in love with Kate Hudson and Matthew McConaughey. Their chemistry was undeniable.

The beloved rom-com is celebrating its 18th anniversary on Feb. 7, and it’s hard to believe it’s been almost 2 decades since the movie came out. Kate and Matthew teamed up again a few years later for another rom-com, but nothing will ever capture the magic between them quite like How To Lose A Guy In 10 Days. In honor of the anniversary, see the cast then and now.

Kate Hudson

Kate Hudson, 41, starred as the one and only Andie Anderson in How To Lose A Guy In 10 Days. The movie elevated her to rom-com queen status. Kate, who is Goldie Hawn’s daughter, went on to star in other rom-coms like Something Borrowed, Bride Wars, and more. She reunited with Matthew for the 2008 rom-com Fool’s Gold. Kate’s also appeared in dramatic films like Deepwater Horizon, Marshall, and Nine. She recently received her second Golden Globe nomination for her performance in the 2021 film Music.

In addition to acting, Kate co-founded the fitness brand Fabletics and has released two books. At the time How To Lose A Guy in 10 Days was released, Kate was married to the Black Crowes frontman Chris Robinson. Their son, Ryder, was born in 2004. Kate and Chris divorced in 2007. Kate got engaged to Muse frontman Matt Bellamy in 2011, and their son, Bingham, was born the same year. Kate and Matt split in 2014. She began dating musician Danny Fujikawa in 2016. Their daughter, Rani Rose, was born in 2018.

Matthew McConaughey

Matthew McConaughey, 51, starred as Benjamin Barry in the 2003 hit rom-com. The actor made quite a name for himself in the rom-com world after How To Lose A Guy In 10 Days. He starred in Ghosts of Girlfriends Past, Failure to Launch, Fool’s Gold, and more. One of his most notable roles was in the 2012 film Magic Mike. Matthew won his first Oscar for his performance in the 2013 film Dallas Buyers Club. His other major movies include Interstellar and The Wolf of Wall Street, as well as the TV show True Detective. He recently appeared in the 2020 film The Gentlemen.

Matthew married Camila Alves in 2012. They have three kids together. Matthew published his memoir, Greenlights, in 2020.

Kathryn Hahn

Kathryn Hahn, 47, played Andie’s best friend, Michelle. She went on to have notable roles in comedies like Anchorman: The Legend of Ron Burgundy, Step Brothers, We’re The Millers, the Bad Moms movies, and more. She earned an Emmy nomination for Outstanding Supporting Actress in a Comedy Series for her role as Rabbi Raquel Fein in Transparent. She’s also starred in the HBO series Mrs. Fletcher and I Know This Much Is True. Kathryn is currently starring as Agnes in the Disney+ series WandaVision. She will star in the Apple TV+ miniseries The Shrink Next Door. Kathryn has been married to Ethan Sandler since 2002. They have two kids together.

Bebe Neuwirth

Bebe Neuwirth, 62, starred as Lana Jong, Andie’s editor. Bebe has had several roles in television, film, and on stage. She played Morticia Addams in The Addams Family on Broadway in 2010. She starred as Nadine Tolliver in the CBS drama Madam Secretary for 4 seasons. She reprised the role she played in the original Jumanji in the 2019 movie Jumanji: The Next Level. Bebe recently played Diana Carlisle in the HBO Max series The Flight Attendant. She is set to star in the upcoming HBO Max series Julia.

Annie Parisse

Annie Parisse, 45, played Andie’s friend, Jeannie, in How To Lose A Guy in 10 Days. She’s had additional roles in movies like National Treasure, Monster-in-Law, Definitely, Maybe, and more. She’s also starred in TV shows like Law & Order, Person of Interest, The Following, and more. Annie recently appeared as Midge Costanza in the FX series Mrs. America. Annie is married to actor Paul Sparks. They have two kids together.

Adam Goldberg

Adam Goldberg, 44, played Ben’s friend and colleague, Tony. Adam has had a number of major roles over the years. He starred as Mr. Numbers in the first season of Fargo. He also starred in TV shows like Joey, Taken, and God Friended Me. His movies since How To Lose A Guy In 10 Days include Zodiac, 2 Days In Paris, and more. He can next be seen in the upcoming CBS series The Equalizer with Queen Latifah. Adam is married to Roxanne Daner, and they have two kids.

Thomas Lennon

Thomas Lennon, 50, played one of Ben’s other colleagues, Thayer. Thomas has had a successful career in front of and behind the camera. One of his biggest projects is that he co-created and starred in the TV series Reno 911! He also starred in the short-lived remake of The Odd Couple. Thomas has voiced a number of characters in animated series over the years. His film roles post-How To Lose A Guy in 10 Days include Hancock, We’re The Millers, Bad Teacher, 17 Again, and more. He was also a writer for films like Baywatch, The Pacifier, and Herbie Fully Loaded. He is set to appear in the upcoming Apple TV+ film Cherry. He is married to Jenny Robertson, and they have a son.

Michael Michele

Michael Michele, 54, starred as Judy Spears, who has a hand in setting up Ben with Andie. Since How To Lose A Guy In 10 Days, Michael has embraced television. She had a recurring role on Gossip Girl in 2011. She played Ayanna Floyd in the FOX series Star from 2017 to 2018. She currently plays the fabulous Dominique Deveraux in The CW’s Dynasty. Season 4 will air in 2021, and the show has already been renewed for season 5. Michael has a son who was born in 2004.

Shalom Harlow

Shalom Harlow, 47, played Judy Green, another associate who sets up Ben with Andie in How To Lose A Guy In 10 Days. On top of acting, Shalom is a famous model. She’s walked runways for Chanel, Prada, Christian Dior, and more. She’s also appeared on the cover of Vogue several times. She notably walked the runway for Versace during Milan Fashion Week in 2018.

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