30+ Adorable Rom-Coms Similar to How to Lose a Guy in 10 Days

If you adore romantic comedies, chances are you’ve seen the beloved 2003 film How to Lose a Guy in 10 Days more times than you can count. This classic features everything you desire in a rom-com: humor, chaotic situations, and of course, love ferns. If you’re on the lookout for more films like How to Lose a Guy in 10 Days, you’re in the right place! While rewatching this gem is always a solid choice, sometimes it’s nice to spice things up with new recommendations. So grab some popcorn, settle in, and get ready to enjoy these enchanting classics.

Movies Similar to How to Lose a Guy in 10 Days

10 Things I Hate About You (1999)
When a strict father requires his anti-social daughter to date before her younger sister can, chaos ensues. Julia and Heath’s characters find themselves in a dating wager that leads to genuine feelings—just like in How to Lose a Guy in 10 Days.
The Proposal (2009)
In this charming film, Sandra Bullock and Ryan Reynolds portray a boss and her assistant who get engaged to dodge deportation. As they pretend to be a couple, they discover real feelings developing between them.
The Ugly Truth (2009)
Katherine and Gerard’s characters clash over their views on relationships, but as they navigate their differences, they gain unexpected insights—especially when it comes to their own feelings.
27 Dresses (2008)
Katherine stars as Jane, a perennial bridesmaid who finally meets her match in journalist Kevin. Their journey together echoes the themes of How to Lose a Guy in 10 Days as feelings grow amidst a backdrop of romance.
Friends With Benefits (2011)
In this modern tale, Mila Kunis and Justin Timberlake start a relationship focused solely on physical intimacy, but soon realize that they might want something deeper—a classic rom-com twist!
Two Weeks Notice (2002)
A passionate lawyer (Sandra Bullock) gives her boss (Hugh Grant) her two weeks’ notice, only to realize they rely on each other more than they thought—both professionally and personally.
While You Were Sleeping (1995)
A transit worker (Sandra Bullock) saves a man, leading his family to believe they’re engaged. Unexpected love blossoms when she falls for his brother, capturing the magic of finding love in unexpected places.
Music and Lyrics (2007)
A washed-up pop star and a plant-watering woman (Hugh Grant and Drew Barrymore) discover chemistry while creating a hit song, blending romance with catchy tunes.
My Best Friend’s Wedding (1997)
Julia Roberts stars as a woman who realizes she loves her best friend just before his wedding, leading to a whirlwind of emotions and laughs.
The Wedding Date (2004)
In an effort to impress her ex, Kat (Debra Messing) hires an escort (Dermot Mulroney) to be her date, leading to unexpected romantic developments.
You’ve Got Mail (1998)
This classic features Meg Ryan and Tom Hanks as rivals who unknowingly fall in love online, showcasing witty banter and sweet moments.
Failure to Launch (2006)
Matthew McConaughey plays a man still living with his parents, leading them to hire a woman (Sarah Jessica Parker) to help him grow up—only for her to fall for him.
The Wedding Planner (2001)
Jennifer Lopez stars as a wedding planner who breaks her own rule by falling for a groom (Matthew McConaughey), creating a delightful romantic conflict.
She’s All That (1999)
A popular jock (Freddie Prinze Jr.) bets he can turn an ordinary girl (Rachael Leigh Cook) into prom queen, only to find himself genuinely attracted to her.
Never Been Kissed (1999)
Drew Barrymore plays a reporter who goes undercover in high school, leading to romantic complications that Andie Anderson would totally understand.
Fool’s Gold (2008)
While not a traditional rom-com, this adventure features Matthew McConaughey and Kate Hudson as a couple searching for lost treasure, filled with romantic tension.
50 First Dates (2004)
In this Adam Sandler classic, a woman loses her memory every day, leading to a unique and hilarious love story.

More Rom-Coms to Consider

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

If you loved How to Lose a Guy in 10 Days, there’s a treasure trove of romantic comedies waiting for you! From charming misunderstandings to heartfelt connections, these films capture the magic of love and laughter. So, whether you’re in the mood for a classic or something a little different, these picks are sure to deliver the rom-com satisfaction you crave.