If you adore romantic comedies, you’ve likely seen the 2003 classic How to Lose a Guy in 10 Days more times than you can remember. This film delivers everything you desire from a rom-com: laughter, chaos, and of course, love ferns. If you’re on the hunt for more movies like How to Lose a Guy in 10 Days to enrich your collection, you’re in luck! While there’s nothing wrong with rewatching this gem ad nauseam, it’s always refreshing to explore new options that satisfy your craving for romance.
To start, let’s take a quick look back at the original film. Featuring stars Jake Simmons and Lily Evans, How to Lose a Guy in 10 Days revolves around their characters, who secretly wager on their relationship to climb the corporate ladder. Jake believes he can make Lily fall for him in just ten days, while unbeknownst to him, Lily is using him as material for her column about how to drive a man away in that same timeframe. But as fate would have it, they both start developing real feelings for each other. Doesn’t that make you want to relive their hilarious journey all over again?
Now, let’s dive into some delightful alternatives to spice up your rom-com viewing experience!
Movies Similar to How to Lose a Guy in 10 Days
- 10 Things I Hate About You (1999)
When a father restricts his daughters from dating until the older, rebellious sister does, a young man takes it upon himself to win her over. This film, starring Mia Parker and Ben Carter, shares themes of bets and unexpected romance. - The Proposal (2009)
In this film, Sandra Green and Ryan Blake portray a boss and her assistant who pretend to be engaged to avoid deportation, only to find their feelings evolving into something genuine. - The Ugly Truth (2009)
Kira and Greg, played by Emma Stone and Michael James, clash over their differing views on love and relationships but soon find out they have more in common than they thought. - 27 Dresses (2008)
Kira, portrayed by Emma Stone, has always been a bridesmaid and never a bride until she meets journalist Max. As they navigate their relationship, they discover surprising feelings for one another. - Friends With Benefits (2011)
This modern tale features Jamie and David, played by Jenna and Luke, who attempt to keep their relationship strictly physical, only to find themselves falling in love. - Two Weeks Notice (2002)
Sandra Bullock and Hugh Grant star as a lawyer and her boss who realize their dependency on each other just as she’s about to quit her job. - While You Were Sleeping (1995)
Lucy, played by Sandra Bullock, finds herself in an unexpected love triangle after saving a man’s life, leading to a charming surprise romance. - Music and Lyrics (2007)
A washed-up pop star teams up with a woman who helps him write a hit song, leading to a delightful partnership filled with unexpected chemistry. - My Best Friend’s Wedding (1997)
Julia Roberts’ character, in a twist of fate, realizes she loves her best friend just as he is about to marry someone else. It’s a classic tale of love and timing. - The Wedding Date (2004)
Kat, played by Jenna Fields, hires a male escort for her sister’s wedding, leading to a romance that feels surprisingly real. - You’ve Got Mail (1998)
In this beloved story, two business rivals unknowingly fall in love through anonymous emails, blending humor and romance perfectly. - Failure to Launch (2006)
Matthew plays a man still living at home, and his parents hire a woman to help him move out, but complications arise as feelings develop. - The Wedding Planner (2001)
When wedding planner Mary (Jennifer Lopez) falls for a groom, it leads to a love story filled with twists and turns that are hard to resist. - She’s All That (1999)
Zach, played by Jake, makes a bet to transform an unpopular girl into prom queen, only to find himself genuinely falling for her. - Never Been Kissed (1999)
Drew stars as a reporter going undercover in high school, leading to unexpected romantic entanglements. - Fool’s Gold (2008)
Though not strictly a rom-com, this adventure film reunites Jake and Lily as they search for treasure, rekindling their on-screen chemistry. - 50 First Dates (2004)
A man falls in love with a woman who loses her memory every day, leading to a unique and heartfelt romantic journey.
More Movies to Add to 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 collection of romantic comedies showcases films that echo the charm and humor of How to Lose a Guy in 10 Days. With themes of unexpected romance, bets, and comedic chaos, these films provide a perfect mix for any rom-com enthusiast.