12 Comedies You’ll Love If You Enjoyed How to Lose a Guy in 10 Days
If you’re a fan of the witty and playful romantic antics in How to Lose a Guy in 10 Days, you’re in for a treat. The combination of sharp humor, charming chemistry between the leads, and the classic “battle of the sexes” trope makes this film unforgettable. Looking for more movies that mix romance, laughter, and a little bit of mischief? Here are 12 movies like How to Lose a Guy in 10 Days that will keep you entertained with their delightful stories of love, misunderstandings, and happy endings.
1. The Proposal (2009)
The Proposal pairs Sandra Bullock and Ryan Reynolds in a hilarious rom-com about an icy boss who forces her assistant to marry her to avoid deportation. What starts as a fake engagement soon turns into real feelings, as the two get to know each other during a trip to Alaska. The sizzling chemistry, misunderstandings, and laugh-out-loud moments make it a perfect pick for fans of How to Lose a Guy in 10 Days. This movie’s blend of humor and heart is sure to win over any rom-com lover.
2. 27 Dresses (2008)
For those who love the romantic tension and chaotic energy of How to Lose a Guy in 10 Days, 27 Dresses is a perfect fit. Katherine Heigl stars as a woman who’s been a bridesmaid 27 times, but her own love life is a mess. Enter James Marsden, a cynical writer who becomes her love interest. The film balances humor and romance while poking fun at wedding culture, making it another charming addition to your rom-com collection.
3. Sweet Home Alabama (2002)
Reese Witherspoon shines as a New York fashion designer who must return to her small Southern town to finalize her divorce from her high school sweetheart. The romantic triangle and Witherspoon’s infectious charm make Sweet Home Alabama an irresistible rom-com. Like How to Lose a Guy in 10 Days, it combines witty banter with moments of heartfelt emotion as the characters navigate love and second chances.
4. 10 Things I Hate About You (1999)
This modern take on Shakespeare’s The Taming of the Shrew is full of sharp dialogue, teen angst, and an unforgettable romance between Heath Ledger and Julia Stiles. The film’s humor, high school setting, and the chemistry between the leads make it an all-time rom-com favorite. Much like How to Lose a Guy in 10 Days, it explores the tension and comedy of two people pretending they don’t care, only to fall in love.
5. Failure to Launch (2006)
Matthew McConaughey returns in another rom-com as a man who refuses to leave his parents’ home. Enter Sarah Jessica Parker, hired to give him a push toward independence, but naturally, feelings start to get in the way. The film’s combination of quirky characters, romance, and hilarious situations offers a fun ride for those who love How to Lose a Guy in 10 Days. The premise of love sneaking up when least expected is a theme both films share.
6. Two Weeks Notice (2002)
Two Weeks Notice pairs Sandra Bullock and Hugh Grant in a story of a brilliant lawyer (Bullock) who decides to quit working for her egotistical and charming boss (Grant). Their love-hate relationship evolves into something more, with plenty of humorous moments and witty repartee. Much like How to Lose a Guy in 10 Days, this movie blends professional tension with romance, making it a lighthearted and fun watch.
7. He’s Just Not That Into You (2009)
Based on the popular self-help book, He’s Just Not That Into You explores modern-day dating with an ensemble cast of characters all trying to figure out love. With stars like Jennifer Aniston, Ben Affleck, and Scarlett Johansson, the film navigates the highs and lows of relationships with humor and heart. If you liked the misunderstandings and romantic entanglements in How to Lose a Guy in 10 Days, this film will keep you entertained with its multiple storylines and relatable characters.
8. Crazy, Stupid, Love (2011)
Crazy, Stupid, Love is a romantic comedy that strikes the perfect balance between humor and heartfelt emotion. Steve Carell plays a man who’s thrown back into the dating scene after his marriage falls apart, while Ryan Gosling steals the show as his smooth-talking wingman. With its witty dialogue and lovable characters, this film has all the elements that make How to Lose a Guy in 10 Days so much fun—misunderstandings, love, and plenty of laughs.
9. The Ugly Truth (2009)
The Ugly Truth is another battle of the sexes rom-com where opposites attract. Katherine Heigl plays a TV producer who reluctantly works with a chauvinistic relationship expert (Gerard Butler) to improve her dating life. What follows is a hilarious, no-holds-barred exploration of dating, love, and relationships. Fans of How to Lose a Guy in 10 Days will enjoy the verbal sparring and undeniable chemistry between the leads in this entertaining rom-com.
10. Something’s Gotta Give (2003)
Something’s Gotta Give pairs Jack Nicholson and Diane Keaton in a more mature love story, full of sharp dialogue and laugh-out-loud moments. Keaton plays a successful playwright who unexpectedly falls for Nicholson’s much older bachelor character. With its witty script and relatable exploration of love in later life, this film is a great pick for fans who appreciate romantic comedies with strong character development.
11. The Wedding Planner (2001)
Jennifer Lopez and Matthew McConaughey star in The Wedding Planner, a romantic comedy about a wedding planner who falls in love with her client. This charming and lighthearted film mirrors the romantic tension and playful humor of How to Lose a Guy in 10 Days. With its love-at-first-sight twist and plenty of wedding mishaps, The Wedding Planner is a feel-good film perfect for fans of rom-coms.
12. Hitch (2005)
Will Smith plays the ultimate dating coach in Hitch, a film that’s equal parts comedy and romance. He helps awkward men woo the women of their dreams, but his own love life becomes a hilarious disaster when he meets Eva Mendes’ character. Hitch is a fun, feel-good movie filled with laugh-out-loud moments and romantic misadventures, making it an excellent choice for fans of How to Lose a Guy in 10 Days.
If you loved the mix of humor, romance, and emotional growth in How to Lose a Guy in 10 Days, these 12 movies will keep you smiling. From playful love-hate relationships to heartfelt connections, these films are guaranteed to offer hours of entertainment. For more romantic comedy recommendations, check out the full list of 22 Best Movies like Eyes Wide Shut | Similar-List and discover even more gems to add to your must-watch list.
Also Read: Why Post-Construction Cleaning is Essential for New Spaces
