How to Lose a Guy in 10 Days is a classic romantic comedy that perfectly blends humor, romance, and a bit of playful deceit. If you loved the cat-and-mouse dynamic between Andie (Kate Hudson) and Ben (Matthew McConaughey) as they try to outwit each other, you’re in for a treat. Whether it’s witty banter, clever schemes, or feel-good love stories, this list of 14 rom-coms has everything to satisfy your craving for more charming, laugh-out-loud romantic films. Let’s dive into these heartwarming and humorous films that share the same playful spirit as How to Lose a Guy in 10 Days.
1. 10 Things I Hate About You (1999)
This modern-day retelling of Shakespeare’s The Taming of the Shrew stars Julia Stiles and Heath Ledger as the rebellious Kat and the charming Patrick. The movie thrives on sharp dialogue, teenage angst, and romantic tension, much like How to Lose a Guy in 10 Days. If you enjoyed the characters’ witty back-and-forth in the latter, you’ll love the clever repartee and love-hate relationship in 10 Things I Hate About You. The chemistry between the leads and the high school setting add to its charm, making it a timeless rom-com.
2. The Proposal (2009)
Sandra Bullock and Ryan Reynolds star in The Proposal, a hilarious romantic comedy about a high-powered boss who forces her assistant to marry her to avoid deportation. Much like How to Lose a Guy in 10 Days, the characters’ relationship begins with a game of deception but soon evolves into genuine affection. Bullock’s uptight, demanding character and Reynolds’ laid-back charm make for an entertaining opposites-attract dynamic. As their fake relationship turns real, the film delivers plenty of laughs and heartwarming moments.
3. The Ugly Truth (2009)
If you enjoyed the battle of the sexes in How to Lose a Guy in 10 Days, The Ugly Truth will be right up your alley. Katherine Heigl and Gerard Butler play two people with opposing views on relationships—Heigl’s character believes in love, while Butler’s character is a cynic. The movie’s central premise, filled with witty banter and underlying attraction, will remind you of the playful scheming in How to Lose a Guy in 10 Days. It’s a fun, laugh-out-loud movie about discovering love when you least expect it.
4. Sweet Home Alabama (2002)
Sweet Home Alabama follows Reese Witherspoon as a successful New York fashion designer who must return to her Southern roots to finalize her divorce. Like How to Lose a Guy in 10 Days, this film features a protagonist with a complicated love life, caught between her past and present relationships. The film is full of Southern charm, humorous moments, and heartfelt romance, making it a perfect pick for fans of lighthearted rom-coms with emotional depth.
5. What Happens in Vegas (2008)
Starring Cameron Diaz and Ashton Kutcher, What Happens in Vegas is a rom-com about two strangers who get married in Las Vegas after a night of drunken fun, only to realize they’ve won a massive jackpot. Much like How to Lose a Guy in 10 Days, the movie’s premise revolves around two people who start out as adversaries but eventually fall for each other. The film’s comedic situations and the undeniable chemistry between Diaz and Kutcher make it a perfect addition to your rom-com watchlist.
6. 27 Dresses (2008)
If you loved How to Lose a Guy in 10 Days for its mix of humor, romance, and strong female lead, 27 Dresses is a must-watch. Katherine Heigl plays a perpetual bridesmaid who’s always helping others with their weddings but struggles with her own love life. The movie captures the humor and frustration of navigating relationships, much like How to Lose a Guy in 10 Days, and offers a heartfelt story about finding love when you least expect it.
7. He’s Just Not That Into You (2009)
This ensemble rom-com offers multiple perspectives on love, dating, and relationships. With a star-studded cast that includes Jennifer Aniston, Ginnifer Goodwin, and Bradley Cooper, He’s Just Not That Into You explores the complexities of modern relationships, much like How to Lose a Guy in 10 Days. The film’s witty take on dating and love makes it a fun and relatable watch for anyone who enjoys romantic comedies.
8. Crazy, Stupid, Love (2011)
Crazy, Stupid, Love combines humor, romance, and a heartwarming story about rediscovering love. Starring Steve Carell, Ryan Gosling, and Emma Stone, the film follows multiple characters as they navigate their love lives. Like How to Lose a Guy in 10 Days, it features clever dialogue, hilarious situations, and characters trying to figure out what they really want in love. The movie’s balance of comedy and emotion will keep you engaged from start to finish.
9. Clueless (1995)
Clueless is a timeless teen rom-com about fashion, friendship, and finding love in the most unexpected places. Starring Alicia Silverstone as the fashionable and well-meaning Cher, the movie’s clever humor and sharp social commentary make it a standout. If you enjoyed the lighthearted tone and playful romance of How to Lose a Guy in 10 Days, Clueless offers a similar blend of humor and heart.
10. Failure to Launch (2006)
Starring Matthew McConaughey and Sarah Jessica Parker, Failure to Launch centers on a man who refuses to move out of his parents’ home and the woman hired to help push him toward independence. Like How to Lose a Guy in 10 Days, the film’s romantic plot is driven by a hidden agenda that leads to unexpected feelings. The movie’s mix of humor and romance, coupled with McConaughey’s charm, makes it an enjoyable watch for fans of rom-coms with a twist.
11. Leap Year (2010)
Leap Year is a charming rom-com about a woman who travels to Ireland to propose to her boyfriend on Leap Day, only to find herself falling for someone else along the way. The movie’s picturesque setting, quirky characters, and humorous situations make it a delightful watch. Like How to Lose a Guy in 10 Days, it’s a story about love found in the most unexpected places, with plenty of laughs along the way.
12. Two Weeks Notice (2002)
Sandra Bullock and Hugh Grant star in Two Weeks Notice, a romantic comedy about a quirky lawyer and her charming but self-centered boss. As Bullock’s character decides to quit her job, the two realize their feelings for each other. The film’s witty dialogue, strong performances, and opposites-attract dynamic make it a perfect companion to How to Lose a Guy in 10 Days. It’s a feel-good movie with plenty of laughs and heartwarming moments.
13. The Wedding Planner (2001)
Jennifer Lopez and Matthew McConaughey star in The Wedding Planner, a rom-com about a wedding planner who falls in love with the groom of one of her clients. Like How to Lose a Guy in 10 Days, this film revolves around characters who initially try to avoid love but find themselves drawn to each other. The movie’s mix of humor, romance, and charming performances make it a classic in the rom-com genre.
14. The Holiday (2006)
The Holiday is a heartwarming rom-com about two women who swap homes for the holidays and end up finding love in unexpected places. Starring Cameron Diaz, Kate Winslet, Jude Law, and Jack Black, the film offers a delightful mix of humor, romance, and emotional depth. Like How to Lose a Guy in 10 Days, it’s a story about love, personal growth, and the surprises life can bring. The film’s charming characters and cozy atmosphere make it a perfect romantic comedy for any season.
If you enjoyed the humor, romance, and playful twists of How to Lose a Guy in 10 Days, these 14 movies will keep you entertained with their delightful rom-com charm. Whether it’s fake relationships, opposites-attract dynamics, or the hilarious consequences of meddling in love, each of these films offers something special. For more rom-com recommendations, check out “Discover 10 Rom-Com Movies Like How to Lose a Guy in 10 Days” or explore other genres, like “Explore Chilling Movies Like As Above So Below | similar-list” for a different kind of cinematic adventure.
