If you’re a fan of romantic comedies filled with hilarious situations, lovable characters, and heartwarming endings, then How to Lose a Guy in 10 Days is probably one of your favorites. This iconic rom-com combines humor, charm, and clever storytelling, making it a timeless classic. If you’re searching for movies that offer a similar mix of romance and comedy, look no further. Here’s a list of 15 movies like How to Lose a Guy in 10 Days that will keep you entertained and leave you smiling. As a bonus, if you enjoy variety, you might also find surprises reminiscent of movies like Michael Clayton, with their intricate narratives and memorable characters.
1. 27 Dresses (2008)
Katherine Heigl shines as Jane, a perennial bridesmaid struggling to find love while planning weddings for others. Her journey becomes complicated when her sister falls for the man Jane secretly loves.
Why You’ll Love It:
Just like Andie Anderson’s witty and relatable personality in How to Lose a Guy in 10 Days, Jane’s charm and self-discovery journey make this a delightful watch. The film is full of humorous scenarios and heartfelt moments, especially when Jane confronts her true feelings and embraces her individuality.
2. The Proposal (2009)
Sandra Bullock and Ryan Reynolds star in this hilarious rom-com about a boss and her assistant pretending to be engaged to save her from deportation.
Why You’ll Love It:
The dynamic chemistry and funny power struggle between Bullock and Reynolds mirror the playful banter in How to Lose a Guy in 10 Days. It’s a perfect mix of comedy and heartfelt romance.
3. 10 Things I Hate About You (1999)
A modern adaptation of Shakespeare’s The Taming of the Shrew, this film stars Heath Ledger and Julia Stiles in a high-school rom-com with sharp wit and unforgettable moments.
Why You’ll Love It:
The humorous push-and-pull relationship between the lead characters offers the same delightful tension as Andie and Ben’s antics.
4. Crazy, Stupid, Love (2011)
Ryan Gosling, Emma Stone, and Steve Carell deliver a multi-layered romantic comedy that explores love from different perspectives.
Why You’ll Love It:
With its witty dialogue and heartfelt themes, this film captures the complexities of relationships in a way similar to How to Lose a Guy in 10 Days.
5. Clueless (1995)
Alicia Silverstone stars as Cher, a wealthy but kind-hearted teen navigating high school life and love in this classic rom-com.
Why You’ll Love It:
Cher’s journey of self-discovery and comedic missteps resonate with the playful energy found in movies like How to Lose a Guy in 10 Days.
6. She’s All That (1999)
A bet turns into unexpected romance in this iconic rom-com, as a popular high schooler helps transform a shy classmate into prom royalty.
Why You’ll Love It:
This movie captures the charm of two opposites falling in love, much like the dynamic in How to Lose a Guy in 10 Days.
7. Maid in Manhattan (2002)
Jennifer Lopez stars as a hotel maid who accidentally charms a politician in this Cinderella-like tale.
Why You’ll Love It:
The unexpected romance and charming storyline make this film a perfect pick for fans of Andie and Ben’s playful love story.
8. When Harry Met Sally (1989)
This timeless classic explores whether men and women can just be friends, with plenty of humor and romantic tension along the way.
Why You’ll Love It:
The natural chemistry and witty banter between Billy Crystal and Meg Ryan are reminiscent of Andie and Ben’s dynamic.
9. Bridget Jones’s Diary (2001)
Renée Zellweger shines as a quirky woman navigating love, career, and self-doubt in this beloved rom-com.
Why You’ll Love It:
Bridget’s relatable struggles and comedic mishaps echo the charm of How to Lose a Guy in 10 Days.
10. My Big Fat Greek Wedding (2002)
A quirky family and unexpected romance collide in this heartwarming and hilarious tale.
Why You’ll Love It:
The cultural humor and sweet love story make this film a feel-good gem for rom-com lovers.
11. Notting Hill (1999)
Julia Roberts and Hugh Grant star in this romantic tale of a movie star falling for a humble bookshop owner.
Why You’ll Love It:
The touching romance and lighthearted humor align beautifully with How to Lose a Guy in 10 Days.
12. Love, Actually (2003)
This ensemble rom-com weaves together multiple love stories during the Christmas season.
Why You’ll Love It:
The film’s heartwarming moments and charming characters offer plenty to adore.
13. Something’s Gotta Give (2003)
Jack Nicholson and Diane Keaton deliver a mature and hilarious look at love in this witty rom-com.
Why You’ll Love It:
The film’s clever humor and engaging performances make it a standout.
14. The Holiday (2006)
Two women swap homes and discover unexpected love during the holidays in this feel-good film.
Why You’ll Love It:
Its heartwarming romance and light comedy make it an instant classic, similar to How to Lose a Guy in 10 Days.
15. Two Weeks Notice (2002)
Sandra Bullock and Hugh Grant team up again in this workplace rom-com filled with humor and heartfelt moments.
Why You’ll Love It:
The playful yet romantic dynamic between the leads is perfect for fans of Andie and Ben.
From heartwarming classics to laugh-out-loud moments, these movies like How to Lose a Guy in 10 Days will keep you entertained. Whether it’s the sharp wit of 10 Things I Hate About You or the touching romance of The Holiday, there’s something for everyone on this list. And if you’re in the mood for a deeper story, explore movies like Michael Clayton for a change of pace. Happy watching!