Are you in the mood for a charming rom-com that’s just as delightful as How to Lose a Guy in 10 Days? You’re in luck because the cinematic world is brimming with movies like How to Lose a Guy in 10 Days that will give you all the feels and laughs you’re craving. Whether you’re looking for a cozy movie night or just need a good dose of romantic escapades, these films are sure to hit the spot. Get your popcorn ready, and let’s dive into the world of love, laughter, and those oh-so-relatable dating dilemmas.
Movies Similar to How to Lose a Guy in 10 Days
1. The Wedding Planner
In The Wedding Planner, Jennifer Lopez stars as Mary Fiore, an ambitious and successful wedding planner who ironically has yet to find love herself. When she’s rescued from a near-fatal accident by a handsome doctor (Matthew McConaughey), Mary believes she’s finally met Mr. Right, only to discover he’s the groom in the biggest wedding of her career. This movie captures the same blend of humor and romance that fans of How to Lose a Guy in 10 Days adore, with a dash of dramatic irony that keeps you rooting for love against all odds.
- Stars: Jennifer Lopez, Matthew McConaughey
- Director: Adam Shankman
- Fun Fact: Jennifer Lopez did most of her own stunts in the movie, including the dance sequences.
2. 10 Things I Hate About You
10 Things I Hate About You is a modern retelling of Shakespeare’s The Taming of the Shrew set in a high school context. This film features the late Heath Ledger in a breakout role, alongside Julia Stiles, as they navigate the complicated world of teen romance and expectations. With its sharp wit and heartfelt moments, it’s a classic in its own right and offers a similar mix of humor and love’s challenges that made How to Lose a Guy in 10 Days so endearing.
- Stars: Heath Ledger, Julia Stiles
- Director: Gil Junger
- Fun Fact: The film’s title is taken directly from one of the most memorable scenes where Julia Stiles’s character reads a poem listing the things she hates about Heath Ledger’s character.
3. 13 Going on 30
Imagine waking up to find yourself suddenly in the future with all your childhood dreams fulfilled, only to realize that adult life is not as simple as you thought. That’s the premise of 13 Going on 30, where Jennifer Garner plays a 13-year-old girl trapped in her 30-year-old self’s life. This film is a heartwarming journey of self-discovery and second chances, much like How to Lose a Guy in 10 Days, and it reminds us that true happiness might just be where we least expect it.
- Stars: Jennifer Garner, Mark Ruffalo
- Director: Gary Winick
- Fun Fact: The “Thriller” dance sequence was added to the movie after Jennifer Garner saw a group of extras fooling around with the dance moves on set.
4. The Proposal
When a high-powered book editor faces deportation to her native Canada, she declares she’s engaged to her unsuspecting assistant to stay in the U.S. The Proposal stars Sandra Bullock and Ryan Reynolds in a comedic clash of wills and cultures. This movie shares the same comedic misunderstandings and romantic tension that How to Lose a Guy in 10 Days fans enjoy, making it a perfect addition to your rom-com collection.
- Stars: Sandra Bullock, Ryan Reynolds
- Director: Anne Fletcher
- Fun Fact: The movie was actually filmed in Massachusetts and Rhode Island, not Alaska, where the story is set.
5. 27 Dresses
27 Dresses spins the tale of Jane, played by Katherine Heigl, a perpetual bridesmaid whose own love life is nearly non-existent. When Jane’s younger sister captures the heart of her secret crush, she begins to re-evaluate her “always the bridesmaid” lifestyle. This film resonates with the same romantic comedy charm as How to Lose a Guy in 10 Days, especially with its focus on the complex world of relationships and an endearing lead character who’s easy to root for.
- Stars: Katherine Heigl, James Marsden
- Director: Anne Fletcher
- Fun Fact: Katherine Heigl had to wear 27 different bridesmaid dresses throughout the film, each with its own unique style.
6. What Happens in Vegas
In What Happens in Vegas, Cameron Diaz and Ashton Kutcher star as two strangers who wake up to discover they got married during a night of drunken debauchery in Las Vegas. When a huge jackpot win complicates their quickie divorce, they are forced to coexist to keep the money. This movie captures the humorous battle of the sexes and unexpected romance that makes it a kindred spirit to How to Lose a Guy in 10 Days.
- Stars: Cameron Diaz, Ashton Kutcher
- Director: Tom Vaughan
- Fun Fact: The story was originally titled “What Happens in Vegas, Stays in Vegas,” but was shortened to the current title.
7. Failure to Launch
Failure to Launch follows the life of a charming 35-year-old man, played by Matthew McConaughey, who still lives with his parents. To get him out of the house, his parents hire a woman (Sarah Jessica Parker) to give him a little push. This romantic comedy features a similar blend of quirky characters and unconventional love stories as How to Lose a Guy in 10 Days, making it a great choice for fans of the genre.
- Stars: Matthew McConaughey, Sarah Jessica Parker
- Director: Tom Dey
- Fun Fact: The film includes several live animals as part of the storyline, including a mockingbird, dolphin, and chipmunk.
8. The Ugly Truth
In The Ugly Truth, Katherine Heigl plays a romantically challenged morning show producer whose show is taken over by Gerard Butler’s chauvinistic TV personality. The film explores the battle of the sexes and the idea that opposites attract, much like the dynamic in How to Lose a Guy in 10 Days. The chemistry between the leads and the humorous take on modern relationships are sure to entertain.
- Stars: Katherine Heigl, Gerard Butler
- Director: Robert Luketic
- Fun Fact: The film’s two leads previously worked together in the animated film “The Tale of Despereaux.”
9. Sweet Home Alabama
Sweet Home Alabama features Reese Witherspoon as Melanie Carmichael, a New York fashion designer who must confront her past in the Deep South before she can marry the city’s most eligible bachelor. This romantic comedy has the charm and wit that resonates with fans of How to Lose a Guy in 10 Days, showcasing a protagonist caught between two worlds and two loves.
- Stars: Reese Witherspoon, Josh Lucas, Patrick Dempsey
- Director: Andy Tennant
- Fun Fact: The coonhound cemetery scene was inspired by the real-life Key Underwood Coon Dog Memorial Graveyard in Alabama.
Monster-In-Law showcases the comedic talents of Jennifer Lopez and Jane Fonda in a story about a woman who meets the perfect man, only to discover his mother is the mother-in-law from hell. This film delivers laughs and relatable family dynamics, akin to the romantic entanglements seen in How to Lose a Guy in 10 Days. The battle for love against a hilariously overbearing adversary will surely entertain fans of the genre.
- Stars: Jennifer Lopez, Jane Fonda, Michael Vartan
- Director: Robert Luketic
- Fun Fact: Monster-In-Law marked Jane Fonda’s return to cinema after a 15-year absence.
11. Just Like Heaven
In Just Like Heaven, Reese Witherspoon plays Elizabeth, a hard-working doctor who ends up in a coma and returns as a spirit to find her apartment occupied by a lonely architect, played by Mark Ruffalo. The two form an unlikely connection that transcends the physical world. This romantic comedy shares the whimsical charm and unique love story that fans of How to Lose a Guy in 10 Days will appreciate.
- Stars: Reese Witherspoon, Mark Ruffalo
- Director: Mark Waters
- Fun Fact: The movie is based on the French novel “If Only It Were True” by Marc Levy.
12. Confessions of a Shopaholic
Confessions of a Shopaholic stars Isla Fisher as Rebecca Bloomwood, a fashionista with a shopping addiction who lands a job at a financial magazine. The film combines the humorous pitfalls of love and luxury, much like the relationship dynamics and comedic elements of How to Lose a Guy in 10 Days. It’s a story about finding true love and the real joys of life amidst a world of material temptations.
- Stars: Isla Fisher, Hugh Dancy
- Director: P.J. Hogan
- Fun Fact: The “Shopaholic” series of books, by Sophie Kinsella, inspired the film.
13. Love Actually
Love Actually explores the complexities of love through various interlinked stories set during the Christmas season in London. This ensemble cast weaves together tales of romance that range from heartwarming to bittersweet. With its charming British humor and poignant moments, Love Actually captures the spirit of How to Lose a Guy in 10 Days by showing love in all its forms.
- Stars: Hugh Grant, Emma Thompson, Alan Rickman, and many others
- Director: Richard Curtis
- Fun Fact: The film features an ensemble cast of British actors and has become a holiday viewing staple for many.
14. Sex And The City
The film Sex And The City continues the story of the four iconic characters from the beloved TV series as they navigate love, friendship, and fashion in New York City. With its witty dialogue and exploration of romantic relationships, the film shares the same urban charm and sassy humor that made How to Lose a Guy in 10 Days a hit.
- Stars: Sarah Jessica Parker, Kim Cattrall, Kristin Davis, Cynthia Nixon
- Director: Michael Patrick King
- Fun Fact: The movie includes countless fashion ensembles, with the wardrobe budget reportedly being around $10 million.
15. A Perfect Pairing
A Perfect Pairing is a delightful romantic comedy that follows a hardworking LA wine-company executive who travels to an Australian sheep farm to land a major client, only to be met with unexpected challenges and a rugged local who challenges her expectations. This film’s blend of career ambitions, cultural contrasts, and unexpected romance captures the same engaging essence that fans of How to Lose a Guy in 10 Days will surely enjoy.
- Stars: Victoria Justice, Adam Demos
- Director: Stuart McDonald
- Fun Fact: The movie was filmed in Queensland, Australia, showcasing the region’s stunning landscapes.
16. The Hating Game
The Hating Game explores the thin line between love and hate as two competing colleagues with clashing personalities find themselves drawn to each other. Based on the bestselling novel by Sally Thorne, this film offers the same kind of witty banter and romantic tension that makes How to Lose a Guy in 10 Days so enjoyable, making it a must-watch for those who love their romance with a side of rivalry.
- Stars: Lucy Hale, Austin Stowell
- Director: Peter Hutchings
- Fun Fact: The film is an adaptation of Sally Thorne’s debut novel, which became a massive hit among romance readers for its sharp dialogue and charismatic leads.
17. I Want You Back
In I Want You Back, two heartbroken strangers, played by Charlie Day and Jenny Slate, team up to sabotage their exes’ new relationships and win them back. The film’s comedic take on post-breakup schemes and the unexpected connections that form as a result will resonate with How to Lose a Guy in 10 Days fans, offering a modern twist on romantic comedy tropes.
- Stars: Charlie Day, Jenny Slate
- Director: Jason Orley
- Fun Fact: The movie was produced by Amazon Studios and released directly on their streaming platform, Amazon Prime Video.
In the end, whether you’re looking for a film filled with laughter, love, or a little bit of both, this collection of movies like How to Lose a Guy in 10 Days offers something for every rom-com aficionado. Each movie brings its own unique flavor to the classic romantic comedy recipe, ensuring that your next movie night will be just as entertaining and heartwarming as Andie and Ben’s hilariously twisted love story. So grab some popcorn, get cozy, and enjoy these delightful movies like How to Lose a Guy in 10 Days.