Movies Like How to Lose a Guy in 10 Days

8 Most Iconic Rom-com Movies Like How to Lose a Guy in 10 Days

Picture this: It’s a rainy Sunday afternoon, and I find myself curled up on the couch, wrapped in a cozy blanket. The room is dimly lit, the aroma of freshly brewed coffee fills the air, and I’m about to hit play on “How to Lose a Guy in 10 Days” for the umpteenth time.

Just as Matthew McConaughey‘s charming smile graces the screen, it hits me—why not explore the cinematic universe for movies with the same magic? That’s when I decided to embark on a quest to find movies like “How to Lose a Guy in 10 Days,” and let me tell you, the rom-com world did not disappoint.

So, if you’re in search of films that capture that same blend of humor, romance, and drama, you’ve come to the right place. Buckle up, rom-com aficionados; you’re in for a treat!

Table of Information About Movies Like How to Lose a Guy in 10 Days:

Movie TitleSimilaritiesDifferencesAvailable On
The ProposalRelationship based on deceptionSet in AlaskaNetflix
Bridget Jones’s DiaryJournalist protagonist, complicated love lifeBroader look at lifeHulu
Crazy, Stupid, LoveComplexities of loveMultiple intersecting relationshipsAmazon Prime
What Happens in VegasRelationship due to comedic eventsAccidental marriageNetflix
The Ugly TruthRelationship based on deceptionOne party is initially cluelessHulu
27 DressesComplicated romantic situationsFocus on self-discoveryAmazon Prime
How to Be SingleSet in New York City, modern datingJourney of self-discoveryNetflix
The Wedding DateRelationship starts as a business arrangementSetting of a weddingHulu
No Strings AttachedComplexities of modern relationshipsChallenges of a “friends with benefits”Amazon Prime
Movies like How to Lose a Guy in 10 Days

Why “How to Lose a Guy in 10 Days” is a Rom-Com Classic

Let’s take a stroll down memory lane, shall we? Released in 2003, this film became an instant classic, thanks to its irresistible blend of humor, romance, and, of course, drama. Who could forget the iconic “love fern” or the hilarious antics of Andie (Kate Hudson) as she tries to drive Ben (Matthew McConaughey) away? It’s a movie that’s as timeless as love itself.

The Search for Movies with the Same Magic

Finding a movie that can hold a candle to “How to Lose a Guy in 10 Days” is no small feat. But fear not, fellow rom-com lovers, for I have scoured the cinematic universe to bring you a list of films that will give you all the feels. From laugh-out-loud moments to heartwarming confessions, these movies have it all.

Movies Like How to Lose a Guy in 10 Days

1. The Proposal

The Proposal

“The Proposal” is a 2009 rom-com starring Sandra Bullock as Margaret, a high-powered book editor who faces deportation to Canada. Her solution? Convince her assistant, played by Ryan Reynolds, to marry her. What ensues is a hilarious trip to Alaska to meet the family and convince them that their love is real.

Why It’s Similar

Much like Andie and Ben, Margaret and Andrew enter into a relationship based on deception, only to find themselves entangled in the web of love.

Why It’s Different

While “How to Lose a Guy in 10 Days” is set in the bustling city of New York, “The Proposal” takes us to the scenic landscapes of Alaska. Plus, there’s a hilarious scene involving a dog and an eagle that you won’t find in any other rom-com.

Also read: 10 Movies Like Sweet Home Alabama That Will Make You Believe in Love Again

2. Bridget Jones’s Diary

Bridget Jones's Diary

“Bridget Jones’s Diary” is a 2001 romantic comedy that follows the life of Bridget Jones, a thirty-something Londoner who decides to take control of her life, starting with a diary. As she navigates her career, friendships, and love life, she finds herself torn between her boss Daniel Cleaver and family friend Mark Darcy.

Why It’s Similar

Just like Andie, Bridget is a journalist, and her love life is as complicated as it gets. Both movies explore the ups and downs of modern relationships, complete with misunderstandings and comedic twists.

Why It’s Different

While “How to Lose a Guy in 10 Days” focuses on a single relationship and its ensuing chaos, “Bridget Jones’s Diary” offers a broader look at life, love, and the pursuit of happiness.

3. Crazy, Stupid, Love

Crazy, Stupid, Love
Image Source: IMDb

In “Crazy, Stupid, Love,” Steve Carell plays Cal, a man whose life unravels after his wife asks for a divorce. Enter Jacob, a suave ladies’ man played by Ryan Gosling, who takes Cal under his wing to teach him the art of seduction. But as they say, love is never straightforward.

Why It’s Similar

Both movies delve into the complexities of love and relationships, albeit from different angles. While “How to Lose a Guy in 10 Days” is a battle of the sexes, “Crazy, Stupid, Love” is more of a coming-of-age story for adults.

Why It’s Different

The film explores multiple relationships and how they intersect, adding layers of complexity that make it stand apart from the single-story focus of “How to Lose a Guy in 10 Days.”

4. What Happens in Vegas

What Happens in Vegas

“What Happens in Vegas” stars Cameron Diaz and Ashton Kutcher as two strangers who wake up to discover they got married after a night of debauchery in Sin City. When one of them wins a jackpot using the other’s quarter, they’re forced to navigate their accidental marriage.

Why It’s Similar

Much like Andie and Ben, the protagonists find themselves in a relationship due to a series of comedic events. The humor and chemistry between the leads are reminiscent of “How to Lose a Guy in 10 Days.”

Why It’s Different

The setting of Las Vegas adds a unique backdrop to the story, and the concept of an accidental marriage brings its own set of comedic and emotional challenges.

You might also like: 10 Movies Like When Harry Met Sally That’ll Give You All The Feels

5. The Ugly Truth

The Ugly Truth
Image Source: Letterboxd

“The Ugly Truth” features Katherine Heigl as Abby, a romantically challenged TV producer, and Gerard Butler as Mike, a chauvinistic TV host. When their paths cross, Mike promises to help Abby win the man of her dreams if she agrees to follow his “ugly” advice about love.

Why It’s Similar

Both movies explore the theme of people pretending to be something they’re not to achieve a romantic or professional goal. The comedic tension between the leads is palpable, much like in “How to Lose a Guy in 10 Days.”

Why It’s Different

While Andie and Ben are both somewhat aware of the game they’re playing, Abby is initially clueless about Mike’s manipulations, adding a different dynamic to their relationship.

6. 27 Dresses

27 Dresses
Image Source: Prime Video

Jane, played by Katherine Heigl, is the eternal bridesmaid who has been in 27 weddings but never her own. When her sister Tess captures the heart of Jane’s secret crush, she begins to reevaluate her role as the perfect bridesmaid and friend.

Why It’s Similar

Both films delve into the complexities of love and commitment, albeit from different perspectives. Andie and Jane are both women who find themselves in complicated romantic situations due to their own actions or circumstances.

Why It’s Different

“27 Dresses” focuses more on the concept of self-discovery and the sacrifices one makes for love, whereas “How to Lose a Guy in 10 Days” is more about the games people play in relationships.

7. How to Be Single

How to Be Single

Starring Dakota Johnson, Rebel Wilson, and Leslie Mann, “How to Be Single” explores the lives of several individuals navigating love, life, and relationships in New York City. It’s a modern take on the rom-com genre, focusing on the importance of self-love.

Why It’s Similar

Both movies are set in New York City and delve into the intricacies of modern dating. They also share a comedic tone that makes light of the struggles people face in their love lives.

Why It’s Different

“How to Be Single” is less about finding love and more about the journey of self-discovery, making it a unique addition to the rom-com genre.

8. The Wedding Date

The Wedding Date

“The Wedding Date” stars Debra Messing as Kat, a woman who hires a male escort, played by Dermot Mulroney, to pose as her boyfriend at her sister’s wedding. As they navigate through family drama and old flames, they find themselves questioning the nature of their arrangement.

Why It’s Similar

Much like “How to Lose a Guy in 10 Days,” this movie revolves around a relationship that starts as a business arrangement but evolves into something more meaningful. The comedic elements and romantic tension are very much in the same vein.

Why It’s Different

The setting of a wedding adds a different layer of complexity and urgency to the relationship, making it distinct from the more casual, playful tone of “How to Lose a Guy in 10 Days.”

9. No Strings Attached

No Strings Attached
Image Source: Netflix

Starring Natalie Portman and Ashton Kutcher, “No Strings Attached” explores the concept of a “friends with benefits” relationship. Emma and Adam vow to keep their relationship purely physical, but as we all know, love is never that simple.

Don’t Miss: 10 Romantic Comedy Movies Like No Strings Attached That You Just Can’t Miss!

Why It’s Similar

Both movies tackle the complexities of modern relationships and the rules we impose on them. They also share a lighthearted tone and a focus on the chemistry between the leads.

Why It’s Different

While “How to Lose a Guy in 10 Days” explores the beginning stages of a relationship, “No Strings Attached” delves into the challenges of maintaining a relationship without emotional attachment.

The Evolution of Rom-Coms

Rom Com Evolution
Image Source: CNN

How the Genre Has Changed Over the Years

Romantic comedies have come a long way since the days of “When Harry Met Sally” and “Pretty Woman.” The genre has evolved to include more diverse narratives, complex characters, and even some social commentary.

But what makes “How to Lose a Guy in 10 Days” so enduring is its timeless appeal, a quality that many modern rom-coms strive to emulate.

Why “How to Lose a Guy in 10 Days” Still Stands Out

In a world where rom-coms are increasingly focused on social issues and complex dynamics, “How to Lose a Guy in 10 Days” remains a breath of fresh air. Its straightforward, feel-good narrative and memorable characters make it a go-to comfort movie for many, even years after its release.


The timeless appeal of “How to Lose a Guy in 10 Days” makes it a cornerstone in the rom-com genre. While finding a movie that can truly match its magic is a tall order, the films listed in this guide come pretty darn close.

So grab some popcorn, snuggle up on the couch, and let the rom-com marathon begin!


What Makes a Movie Similar to “How to Lose a Guy in 10 Days”?

Movies that capture the same blend of humor, romance, and drama are often considered similar to “How to Lose a Guy in 10 Days.” The chemistry between the leads and the comedic tension are also key factors.

Are There Any Sequels to “How to Lose a Guy in 10 Days”?

Unfortunately, there are no official sequels to the movie, but the enduring popularity of the film has led to numerous speculations and fan-made continuations.

What Are Some Modern Takes on the Classic Rom-Com Formula?

Movies like “Crazy Rich Asians” and “To All the Boys I’ve Loved Before” offer fresh perspectives on the rom-com genre, incorporating diverse casts and modern relationship dynamics.

How Do I Find Movies That Are Similar in Tone and Style?

Streaming platforms often categorize movies by genre and similarity, making it easier to find films that match your taste.

What Are Some Must-Watch Rom-Coms for Fans of “How to Lose a Guy in 10 Days”?

Apart from the movies listed in this article, classics like “Notting Hill,” “10 Things I Hate About You,” and “Love Actually” are must-watches for any rom-com aficionado.

Where Can I Stream Movies Like “How to Lose a Guy in 10 Days”?

Most of these movies are available on popular streaming platforms like Netflix, Hulu, and Amazon Prime Video.

Written by Kanchan

Hey folks, my name is Kanchan! A botanist with a flair for entertainment, celebrity gossips, TV shows, movies and pop culture.