30+ Adorable Movies Similar to How to Lose a Guy in 10 Days

If you’re a romantic comedy enthusiast, chances are you’ve seen the 2003 film How to Lose a Guy in 10 Days more times than you can count. This delightful movie delivers everything a rom-com lover craves: laughs, chaos, and, of course, love ferns. If you’re in the mood for more films that capture that same enchanting spirit, you’re in luck! While there’s nothing wrong with indulging in that classic repeatedly (no judgment here!), sometimes it’s nice to explore other charming options that still satisfy your romantic cravings.

Let’s take a moment to revisit the original film. Starring Ben Mitchell and Anna Rivers, How to Lose a Guy in 10 Days follows their characters, who each secretly bet on their relationship to boost their careers. Ben believes he can make Anna fall in love with him in just 10 days, while Anna uses him as fodder for her latest column — ironically, about how to lose a guy in that timeframe. What they didn’t expect was to truly fall for each other. Isn’t that enough to make you want to relive their hilarious antics once more?

But if you’re ready to switch things up, sit back and enjoy these rom-com gems.

Movies Like How to Lose a Guy in 10 Days

10 Things I Hate About You (1999)
In a classic tale of sibling rivalry, a father restricts dating until his rebellious daughter finds romance. Featuring Julia Stiles and Josh Hartnett, this film mirrors the themes of love wagers and unexpected connections.
The Proposal (2009)
Sandra Bullock and Ryan Reynolds star as a boss and her assistant who fake an engagement to avoid deportation, only to find real feelings blossoming amidst the charade.
The Ugly Truth (2009)
Katherine Heigl and Gerard Butler clash over their differing views on relationships, but their constant bickering evolves into a romance filled with comedic insights.
27 Dresses (2008)
Katherine Heigl plays Jane, a perpetual bridesmaid who finds love in an unexpected place when she meets a handsome journalist played by James Marsden.
Friends With Benefits (2011)
Mila Kunis and Justin Timberlake enter a no-strings-attached relationship, only to discover that true love is hard to keep at bay.
Two Weeks Notice (2002)
Sandra Bullock shines as a lawyer who realizes her true feelings for her boss (Hugh Grant) just as she’s about to quit her job.
While You Were Sleeping (1995)
After saving a man from an accident, Lucy (Sandra Bullock) pretends to be his fiancée, leading to unexpected romance with his brother, Jack (Bill Pullman).
Music and Lyrics (2007)
An unlikely pair, Alex (Hugh Grant) and Sophie (Drew Barrymore), collaborate on a song, igniting chemistry that could revive Alex’s career.
My Best Friend’s Wedding (1997)
Julia Roberts plays Julianne, who realizes she loves her best friend (Dermot Mulroney) just as he’s about to marry someone else. A recipe for comedic disaster ensues!
The Wedding Date (2004)
Debra Messing hires a male escort (Dermot Mulroney) to be her date at a wedding, leading to unforeseen romantic developments.
You’ve Got Mail (1998)
In this classic, Meg Ryan and Tom Hanks navigate their relationship as business rivals who unknowingly connect online, blending humor and heartfelt moments.
Failure to Launch (2006)
Matthew McConaughey stars as a man still living with his parents, where a hired consultant (Sarah Jessica Parker) unexpectedly falls for him.
The Wedding Planner (2001)
Jennifer Lopez plays a wedding planner who violates the golden rule by falling for one of her grooms, portrayed by Matthew McConaughey.
She’s All That (1999)
Freddie Prinze Jr. makes a bet to transform an ordinary girl (Rachael Leigh Cook) into prom royalty, only to discover true feelings along the way.
Never Been Kissed (1999)
Drew Barrymore plays an undercover reporter posing as a high school student, leading to hilarious and heartfelt situations.
Fool’s Gold (2008)
While not a traditional rom-com, this adventure film reunites McConaughey and Hudson as they team up to find buried treasure.
50 First Dates (2004)
In this Adam Sandler classic, a man falls for a woman (Drew Barrymore) who has short-term memory loss, complicating their romance in a unique way.

More Classics to Consider for Your Rom-Com List:

Hitch (2005)
What Happens in Vegas (2008)
Just Go With It (2011)
Made of Honor (2008)
The Holiday (2006)
Leap Year (2010)
Definitely, Maybe (2008)
When in Rome (2010)
Pretty Woman (1990)
What Women Want (2000)
Ghosts of Girlfriends Past (2009)
Only You (1994)
My Best Friend’s Girl (2008)
Someone Like You (2001)
He’s Just Not That Into You (2009)

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Summary

This list of romantic comedies showcases films that share the delightful charm of How to Lose a Guy in 10 Days. With themes of unexpected love and humorous situations, these movies are sure to please any rom-com fan.