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This is what the cast of How to Lose a Guy in 10 Days are all up to now, 20 years on

Matthew McConaughey and Kate Hudson recently reunited on an Instagram live!


Somehow it has been 20 years since one of the greatest romantic comedies ever premiered, How to Lose a Guy in 10 Days. Only the other month, the iconic song You’re So Vain took over our For You Pages and it got us ready for the greatest movie anniversary ever.

While Andie and Benjamin are tasked with very opposite challenges for one another, we still fall in love with their rocky love story. 20 years on, the cast of How to Lose a Guy in 10 Days have gone on to become movie and TV stars, gripping us to screens everyday.

While you make a Paramount Plus account to watch this film over and over again, here’s what the cast of How to Lose a Guy in 10 Days have been up to and what they’re doing now.

Kate Hudson – Andie

How to Lose a Guy in 10 Days cast now

via Instagram @katehudson

Kate Hudson starred as Andie Anderson in the rom com classic and has recently been on our screens in Netflix’s Glass Onion. After How to Lose a Guy in 10 Days, Kate starred in a number of rom coms including Raising Helen, You, Me and Dupree and Fool’s Gold. In 2022, Kate Hudson announced to people that she was releasing music in 2023, and after her performance in Glee, I can’t wait.

After a number of engagements and marriages, Kate is now in a relationship with Danny Fujikawa and they have one child together called Rani. Kate has two other children from her separate relationships in the past.

Matthew McConaughey – Benjamin

Matthew McConaughey was already a well known name before landing the role of Benjamin Barry in How to Lose a Guy in 10 days, but it was this film that catapulted him into romantic comedy stardom. After starring alongside Kate Hudson, Matthew starred in The Wedding Planner, Ghosts of Girlfriends Past and Failure to Launch.

One of Matthew’s most recent projects was in 2019 in the Guy Ritchie movie The Gentlemen. He has been married since 2012 to Camila Alves and they have three children together, Levi, Vida and Livingston. Also in 2019, Matthew was unveiled as one of the four new minority owners of MLS team Austin FC.

Kathryn Hahn – Michelle

How to Lose a Guy in 10 Days cast now

via Instagram @kathrynhahnofficial

One of Matthew’s most recent projects was in 2019 in the Guy Ritchie movie The Gentlemen. He has been married since 2012 to Camila Alves and they have three children together, Levi, Vida and Livingston. Also in 2019, Matthew was unveiled as one of the four new minority owners of MLS team Austin FC.

Kathryn Hahn – Michelle

How to Lose a Guy in 10 Days cast now

via Instagram @kathrynhahnofficial

Kathryn has been married since 2002 to Ethan Sandler and they have two children together called Mae and Leonard. In case you were wondering, Ethan has absolutely zero relation to comedy legend Adam Sandler.

Annie Parisse

Annie played the role of Jeannie, one of Andie’s close Composure friends. After How to Lose a Guy in 10 Days, Annie starred alongside Jennifer Lopez in Monster-in-Law in 2005. Since then, Annie has starred in the TV series Friends from College, The Following and Law & Order.

Annie is married to American actor Paul Sparks and they have one child together, called Emmett and a daughter, Lydia, who was born in 2014.

Thomas Lennon – Thayer

via Instagram @thomaspatricklennon

Thomas Lennon is the heart and soul of any romantic comedy from the early 2000s and always plays an iconic character. Thomas has starred in a handful of major comedies including I Love You, Man, 17 Again and We’re the Millers. Thomas still currently stars in Reno 911 and up until 2017 he starred alongside Matthew Perry in The Odd Couple.

Thomas has been married since 2002 to actress Jenny Robertson, and they have one child together called Oliver.

Adam Goldberg – Tony

Tony is one of Ben’s friends who almost ruins the entire experiment, and is played by Adam Goldberg. Shortly after How to Lose a Guy in Ten Days, Adam went on to star in I Love Your Work, The Hebrew Hammer and Stay Alive. Adam still continues to act and currently stars in the crime series The Equalizer as Harry Keshegian.

Adam is married to artist Roxanne Daner and they have three children together. Before he married Daner, Adam actually dated Christina Ricci for four years from 2003 to 2007.

Michael Michele – Judy Spears

via Instagram @michaelmichelelegit

Another one of the cast members from How to Lose a Guy in 10 Days who is up to some pretty cool things now is Michael Michele. One of Ben’s rivals was Judy Spears and she was played by Michael Michele in the movie. Fans of the movie will recognise Michael for her more recent role in Netflix’s Dynasty as Dominique Deveraux. Michael has also starred in ER, Relative Stranger and Star.

Michael isn’t currently married but she has one son called J. Brandon Rodriguez, who she had with her ex-partner, Jimmy Rodriguez.

Shalom Harlow – Judy Green

via Instagram @shalomharlow

Canadian model Shalom Harlow played the role of Judy Green. Shalom rose to fame in the 1990s and became a supermodel after walking in runway shows for the likes of Yves Saint Laurent, Alexander McQueen and Chanel. Alongside her modelling work, Shalom has starred in a number of films including McQueen, Head Over Heels and The Last Romantic.

Bebe Neuwirth – Lana

Lana was Andie’s tough boss at the magazine and was played by BEbe Neuwirth in How to Lose a Guy in 10 Days. Despite being more well known for her roles on Broadway, Babe has starred in a number of TV drama as and sitcoms including Frasier, Madam Secretary and Cheers. More recently, BEbe starred in Netflix’s Tick, Tick…Boom!

Babe has been married since 2009 to American director, Chris Calkins.

For all the latest Netflix news, drops, quizzes and memes like The Holy Church of Netflix on Facebook. 

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