Movies Like How to Lose a Guy in 10 Days: Romantic Comedy

Embarking on a journey through movies like How to Lose a Guy in 10 Days opens a delightful pandora’s box of romantic comedy gems that promise laughter, love, and the occasional heartfelt tear. This iconic film, known for its charming blend of wit, romance, and memorable mishaps, has set a high bar for the genre, capturing the hearts of audiences worldwide. 

As we dive into this curated collection, we invite you to rekindle the magic of falling in love, the thrill of unexpected twists, and the joy of laughter that echoes through these cinematic treasures. Each film on our list mirrors the enchanting narrative and charismatic appeal in “How to Lose a Guy in 10 Days.” 

The article brings its unique flavor to romantic comedies, ensuring that your movie nights are filled with endless entertainment and heartwarming moments. So, grab your popcorn, cozy up, and explore the world of romantic comedies that continue to steal our hearts, just as “How to Lose a Guy” did.

Movie NameHow to Lose a Guy in 10 Days
ProducerLynda Obst
DirectorDonald Petrie
First ReleaseFebruary 7, 2003
Budget$50 million
Box Office$177.5 million
How To Lose A Guy In 10 Days Plot

20 Movies Like How to Lose A Guy In 10 Days

If you loved the playful romance and laughter in “How To Lose A Guy In 10 Days,” you’ll adore our 20 movies like it. These films are perfect for those looking to watch How To Lose A Guy In 10 Days movies like it, offering a mix of charming love stories, humor, and heartwarming moments that capture the essence of romantic comedies. 

From the classic misunderstandings in “10 Things I Hate About You” to the love-hate dynamics in “The Proposal,” each movie promises a delightful escape into stories where love triumphs in the most unexpected ways. So, grab some popcorn and prepare for a marathon of laughter, love, and mischief with these captivating rom-coms.

10 Things I Hate About You (1999)

Movie Name10 Things I Hate About You (1999)
DirectorGil Junger
ProducerAndrew Lazar
Release DateMarch 31, 1999
Total Budget$13 million
Gross Profit$60.4 million

Dive into the spirited world of “10 Things I Hate About You” (1999), a classic romantic comedy that puts a modern twist on Shakespeare’s “The Taming of the Shrew.” The movie is set in an American high school, the film and spins the tale of the Stratford sisters: popular Bianca, who’s eager to date, and her headstrong, fiercely independent sister Kat. 

The catch? Their strict father’s rule: Bianca can only date if Kat does. Enter Patrick Verona, the mysterious bad boy hired to woo Kat, setting off a series of hilarious and heartwarming events. As Patrick tries to break through Kat’s tough exterior, the movie takes us on a rollercoaster of emotions, from laugh-out-loud moments to touching revelations about love and vulnerability. 

“10 Things I Hate About You” is a delightful journey through the ups and downs of teenage love, filled with witty banter, memorable characters, and the timeless message that love can be found in the most unexpected places.

10 Things I Hate About You (1999)

Friends With Benefits (2011)

Movie NameFriends With Benefits (2011)
DirectorWill Gluck
ProducerLiz Glotzer
Release DateJuly 18, 2011
Total Budget$35 million
Gross Profit$149.5 million

“Friends With Benefits” (2011) offers a fresh take on the complexities of modern relationships, wrapped in a humorous and heartwarming romantic comedy. The story centers around Jamie, a headstrong New York-based headhunter, and Dylan, an art director from Los Angeles, who cross paths professionally. As their friendship blossoms, they add a physical element to their relationship, vowing to keep emotions out of the equation.

What starts as a fun arrangement without the hassle of romantic commitments quickly unfolds into a tangled web of feelings and desires. The film cleverly navigates the thin line between friendship and love, challenging the duo’s initial relationship beliefs. 

With its witty dialogue, charming chemistry between the leads, and comedic yet relatable situations, “Friends With Benefits” explores the age-old question: Can friends keep things physical without falling for each other?

Friends With Benefits (2011)

27 Dresses (2008)

Movie Name27 Dresses (2008)
DirectorAnne Fletcher
ProducerGary Barber
Release DateJanuary 10, 2008
Total Budget$30 million
Gross Profit$165.8 million

“27 Dresses” (2008) charmingly unfolds the story of Jane, an everlasting bridesmaid whose love life takes a backseat to her dedication to being the perfect support for her friends on their big days. With a closet filled with attendant dresses – precisely 27 – Jane’s tale is a heartwarming journey through wedding events, each symbolizing her selfless nature. 

However, her world turns upside down when her younger sister captures the heart of Jane’s secret crush, leading her to question her role as the go-to bridal aide. Amidst the chaos, a cynical yet charismatic journalist, Kevin, enters her life, intent on uncovering the story behind her bridesmaid adventures. 

Jane confronts her fears and desires as they grow closer, leading to delightful twists and turns. “27 Dresses” is a captivating exploration of love, self-discovery, and the true meaning of happiness, all wrapped up in a bouquet of laughter and tender moments. Watch more How to Lose a Guy in 10 Days movies like stuff by viewing this masterpiece.

27 Dresses (2008)

You’ve Got Mail (1998)

Movie NameYou’ve Got Mail (1998)
DirectorNora Ephron
ProducerLauren Shuler Donner
Release DateDecember 18, 1998
Total Budget$65 million
Gross Profit$250.8 million

“You’ve Got Mail” (1998) spins a digital-age romance tale long before swiping right became the norm. Set against the backdrop of New York City, the story brings together Kathleen Kelly, the charming owner of a quaint bookstore, and Joe Fox, the heir to a mega bookstore chain. 

Unknown to each other, their real-life rivalry contrasts sharply with the anonymous online bond, where they pour their hearts out without the constraints of their business battles. As they exchange emails, their virtual connection deepens, leading to poignant revelations about the complexities of love and identity in the digital era. 

The enchanting film cleverly navigates the irony of two adversaries unknowingly finding solace and understanding in each other’s digital personas. “You’ve Got Mail” is one of the similar movies, like How to Lose a Guy in 10 Days.

You've Got Mail (1998)

She’s All That (1999)

Movie NameShe’s All That (1999)
DirectorRobert Iscove
ProducerPeter Abrams
Release DateJanuary 19, 1999
Total Budget$7–10 million
Gross Profit$103.2 million

“She’s All That” (1999) captures the essence of high school transformation tales with a unique twist that keeps viewers hooked from start to finish. The plot centers around Zack Siler, the typical high school heartthrob, who faces the ultimate challenge: transforming the artistic and unassuming Laney Boggs into the prom queen. 

The bet, born out of an ego from a recent breakup, sets the stage for an unexpected journey of self-discovery, friendship, and love. As Zack and Laney’s worlds collide, they uncover truths about themselves and each other, challenging the superficial norms of high school popularity.

The film cleverly navigates the themes of authenticity, acceptance, and the beauty of seeing beyond the surface. “She’s All That” stands out as a heartwarming story that celebrates the power of genuine connections, reminding us that true beauty lies in being unapologetically oneself.

She's All That (1999)

The Wedding Planner (2001)

Movie NameThe Wedding Planner (2001)
DirectorAdam Shankman
ProducerPeter Abrams
Release DateJanuary 26, 2001
Total Budget$28 million
Gross Profit$95 million

“The Wedding Planner” (2001) weaves a delightful narrative around Mary Fiore, San Francisco’s most successful wedding planner, who lives by the rule that you should never mix business with pleasure. However, her well-ordered life faces upheaval when she unexpectedly falls for Steve Edison, a charming pediatrician. 

The twist? He turns out to be the groom in one of her biggest weddings yet. Caught in a brief of professional ethics and burgeoning emotions, Mary must navigate through a maze of wedding chaos, comedic misunderstandings, and her deep feelings. 

The romantic comedy delves into the irony of a wedding planner on the edge of ruining what could be her happy ending. “The Wedding Planner” is a heartwarming tale that explores the unpredictability of love, the importance of taking chances, and the joy that comes from finding love when and where you least expect it.

The Wedding Planner (2001)

The Ugly Truth (2009)

Movie NameThe Ugly Truth (2009)
DirectorRobert Luketic
ProducerTom Rosenberg
Release DateJuly 24, 2009
Total Budget$38 million
Gross Profit$205.3 million

“The Ugly Truth” (2009) delves into the deep world of love and relationships through the eyes of Abby Richter, a romantically challenged morning show producer, and Mike Chadway, her crass yet charismatic new correspondent who vows to prove his theories on relationships. 

Abby’s quest for love is met with comedic misadventures as Mike’s unorthodox methods to woo her dream man challenge her proposed notions of romance. It is set against the backdrop of a bustling TV studio; this film masterfully blends humor, heart, and a hint of tension, leading to unexpected revelations about the nature of attraction and the complexities of the heart. 

“The Ugly Truth” is a witty exploration of the battle of the sexes, the clash between ideals and reality in love, and the unexpected places where we find connection. It’s a romantic comedy that entertains and delves into the truth behind the games people play in the quest for love. Go with this film if you want to enjoy How to Lose a Guy more in 10 Days-like movies.

The Ugly Truth (2009)

The Wedding Date (2005)

Movie NameThe Wedding Date (2005)
DirectorClare Kilner
ProducerJessica Bendinger
Release DateFebruary 4, 2005
Total Budget$15 million
Gross Profit$47.2 million

“The Wedding Date” (2005) presents a charming twist on the classic plus-one difficulty when Kat Ellis, facing the daunting prospect of attending her younger sister’s wedding alone, hires a suave male escort, Nick Mercer, to pose as her boyfriend. It is set against the picturesque backdrop of a lavish London wedding, and the plot thickens as Kat aims to make her ex-fiancé, who’s also the best man, green with envy.

However, as the façade unfolds, Kat and Nick are entangled in a web of unexpected emotions and complicated family dynamics. This romantic comedy skillfully blends humor, romance, and a touch of drama, showcasing the lengths one might go to avoid the dreaded singles table. 

“The Wedding Date” is a heartwarming journey of self-discovery, forgiveness, and how love can redefine our lives. It proves that sometimes, the best relationships start in the most unconventional ways.

The Wedding Date (2005)

My Best Friend’s Wedding (1997)

Movie NameMy Best Friend’s Wedding (1997)
DirectorP. J. Hogan
ProducerJerry Zucker
Release DateJune 20, 1997
Total Budget$38 million
Gross Profit$299.3 million

“My Best Friend’s Wedding” (1997) spins a captivating tale around Julianne Potter, a food critic who realizes she’s in love with her best friend, Michael, only after he announces his impending happy day to the delightful Kimberly. 

Faced with the ticking clock of Michael’s wedding, Julianne embarks on a comedic and heart-fetching quest to win him back, armed with insider knowledge but shadowed by her conflicting emotions and the genuine bond between the engaged couple. 

Set to a soundtrack of timeless classics, this romantic comedy cleverly navigates the blurred lines between love, friendship, and rivalry. Julianne’s antics, driven by desperation and devotion, lead to unexpected revelations about love, loyalty, and personal integrity. 

My Best Friend's Wedding (1997)

50 First Dates (2004)

Movie Name50 First Dates (2004)
DirectorPeter Segal
ProducerJack Giarraputo
Release DateFebruary 13, 2004
Total Budget$75 million
Gross Profit$198.5 million

“50 First Dates” (2004) offers a heartwarming spin on romance with its unique storyline, where Henry, a charming veterinarian, falls for Lucy, an art teacher with short-term memory loss that resets her memory every day. 

The movie is set in the picturesque Hawaiian backdrop, and this romantic comedy unfolds as Henry discovers the depth of his feelings for Lucy, committing to win her heart anew each day. This film beautifully blends humor with the challenges of an unconventional relationship, showcasing the power of love in the face of adversity. 

“50 First Dates” is a testament to persistence, creativity in courtship, and the idea that true love is worth fighting for daily, making it a memorable and uplifting cinematic experience.

50 First Dates (2004)

What Happens in Vegas (2008)

Movie NameWhat Happens in Vegas (2008)
DirectorTom Vaughan
ProducerMichael Aguilar
Release DateApril 22, 2008
Total Budget$35 million
Gross Profit$219.3 million

“What Happens in Vegas” (2008) turns a chance encounter into a whirlwind adventure when Joy, a meticulous trader, and Jack, a carefree carpenter, wake up in Las Vegas as unexpected newlyweds after a night of revelry. Their attempt to quickly annul the marriage is thwarted when Jack wins a huge jackpot using Joy’s quarter, binding them together in a battle for the money. 

The movie is set against the vibrant backdrop of Las Vegas and New York, and this comedy explores the chaotic journey of two opposites stuck together by law and luck. As they devise schemes to undermine each other, they unwittingly embark on a path of self-discovery and mutual understanding. “What Happens in Vegas” is a lively tale of uncertainty, love, and the surprising outcomes of life’s unpredictable gambles.

What Happens in Vegas (2008)

Music and Lyrics (2007)

Movie NameMusic and Lyrics (2007)
DirectorMarc Lawrence
ProducerMartin Shafer
Release DateFebruary 14, 2007
Total Budget$40 million
Gross Profit$145.9 million

“Music and Lyrics” (2007) harmonizes the unlikely duo of Alex Fletcher, a washed-up ’80s pop star, and Sophie Fisher, a quirky aspiring lyricist, in a delightful romantic comedy. When Alex is given the golden opportunity to compose a chart-topping hit for a current pop sensation, he needs lyrical inspiration, which he unexpectedly discovers in Sophie. 

The movie is set to a soundtrack that captures the essence of collaboration and creativity; this film explores the melody of love and partnership in music and life. As Alex and Sophie navigate the challenges of the music industry, they compose not just a hit song but also a new chapter in their lives. 

Music and Lyrics (2007)

Just Go with It (2011)

Movie NameJust Go with It (2011)
DirectorDennis Dugan
ProducerAdam Sandler
Release DateFebruary 8, 2011
Total Budget$80 million
Gross Profit$215 million

“Just Go with It” (2011) blends laughter and romance in a plot that spirals from a simple lie into a complex web of deceit. The story follows Danny, a successful plastic surgeon who pretends to be unhappily married to attract women. 

When he meets Palmer, the woman of his dreams, he enlists his loyal assistant, Katherine, as his soon-to-be ex-wife to cover up his long-lasting lying. What starts as a straightforward plan quickly escalates into a hilarious and heartwarming series involving fake family dynamics, unexpected emotions, and a spontaneous trip to Hawaii. 

This comedy masterpiece showcases the unpredictable journey of love, where sometimes, pretending leads to the most genuine connections. “Just Go with It” is a testament to the idea that love can emerge from the most unexpected places, urging us to embrace the chaos with a smile. It is one of the other movies like How to Lose a Guy in 10 Days.

Just Go with It (2011)

Hitch (2005)

Movie NameHitch (2005)
DirectorAndy Tennant
ProducerWill Smith
Release DateFebruary 11, 2005
Total Budget$55-70 million
Gross Profit$371.6 million

“Hitch” (2005) introduces us to Alex “Hitch” Hitchens, New York City’s hidden love guru, who excels in coaching men on how to win the hearts of their affections. His latest project, the awkward and lovestruck Albert, aims to attract the glamorous Allegra Cole. 

However, Hitch’s tried-and-true methods face the ultimate test when he encounters Sara Melas, a savvy gossip columnist immune to his charms. As Hitch navigates the complexities of love, his rules unravel, leading to comedic twists and heartfelt revelations. 

The movie is set against the bustling backdrop of Manhattan. This romantic comedy delves into the irony of a relationship expert struggling in his love life, proving that sometimes the best approach is just to be yourself when it comes to love. “Hitch” is a witty, feel-good movie that reminds us of the unpredictability and joy of falling in love.

Hitch (2005)

Fool’s Gold (2008)

Movie NameFool’s Gold (2008)
DirectorAndy Tennant
ProducerDonald De Line
Release DateFebruary 8, 2008
Total Budget$70 million
Gross Profit$111.2 million

“Fool’s Gold” (2008) is an adventure where treasure hunting and romance collide. The story follows the charismatic Finn and his estranged wife, Tess, as they reunite on a quest to uncover a legendary 18th-century treasure. 

The movie is set against the sparkling backdrop of the Caribbean, and their journey is filled with action, humor, and unexpected twists. As they navigate through a series of clues and compete with rival treasure hunters, Finn and Tess rediscover their lost spark amidst the excitement of the chase. 

The action-packed romantic comedy blends the thrill of discovery with the warmth of rekindled love, proving that the greatest treasures are sometimes found in the most unexpected places. “Fool’s Gold” is a captivating tale of adventure, love, and the appeal of the unknown. This is one of the other good movies like How to Lose a Guy in 10 Days.

Fool's Gold (2008)

While You Were Sleeping (1995)

Movie NameWhile You Were Sleeping (1995)
DirectorJon Turteltaub
ProducerRoger Birnbaum
Release DateApril 21, 1995
Total Budget$17 million
Gross Profit$182 million

“While You Were Sleeping” is a heartwarming romantic comedy from 1995 that captivates audiences with its unique and engaging storyline. The film follows Lucy, a lonely transit worker, who rescues her secret crush, Peter, from an oncoming train. 

With Peter in a coma, a misunderstanding leads Peter’s family to believe Lucy is his fiancée. Lucy finds herself in a comedic web of lies as his family embraces her. The situation gets even more complicated when she falls for Peter’s brother, Jack.

The charming tale combines humor, romance, and a touch of holiday spirit, making it a delightful watch for anyone looking for a feel-good movie experience. The plot’s twists and turns keep viewers engaged, while the heartfelt moments remind us of the importance of family and love.

While You Were Sleeping (1995)

Never Been Kissed (1999)

Movie NameNever Been Kissed (1999)
DirectorRaja Gosnell
ProducerSandy Isaac
Release DateApril 9, 1999
Total Budget$25 million
Gross Profit$84.6 million

“Never Been Kissed” is a delightful 1999 romantic comedy that takes its audience on a nostalgic trip back to high school with a unique twist. The story centers around Josie, a special and unassuming newspaper reporter who gets a second chance at her awkward high school years under the guise of an undercover assignment. 

Furthermore, tasked with insightfully managing a high school, Josie navigates the complex social hierarchies, experiencing all the highs and lows of teenage life over again. Amidst the chaos, she encounters unexpected feelings for her dreamy English teacher. 

This masterpiece film cleverly blends humor, romance, and a touch of drama, making it a must-watch for those who love a good makeover story with a heartfelt message about self-acceptance and the courage to be oneself. This masterpiece provides charming comedy where you can enjoy more movies like How to Lose a Guy in 10 Days.

Never Been Kissed (1999)

Failure to Launch (2006)

Movie NameFailure to Launch (2006)
DirectorTom Dey
ProducerScott Rudin
Release DateMarch 10, 2006
Total Budget$50 million
Gross Profit$130.2 million

“Failure to Launch” is a 2006 romantic comedy that humorously explores adult children living at home. The film stars Matthew McConaughey as Tripp, a charming 30-something with no intention of moving out of his parents’ house. Desperate for some empty nest time, his parents hire Paula, played by Sarah Jessica Parker, a specialist encouraging men to become independent. 

The catch? Paula must make Tripp fall in love with her and motivate him to embrace adulthood. What unfolds is a series of comedic misadventures and unexpected romance. This movie cleverly tackles the theme of late bloomers with a blend of humor and heart, making it an engaging watch for anyone who enjoys a good laugh mixed with a touch of romance.

Failure to Launch (2006)

Two Weeks Notice (2002)

Movie NameTwo Weeks Notice (2002)
DirectorMarc Lawrence
ProducerSandra Bullock
Release DateDecember 20, 2002
Total Budget$60 million
Gross Profit$199 million

“Two Weeks Notice” is a charming, entertaining movie from 2002 that creatively explores the dynamics of a workplace romance with a twist. What follows is a cleverly crafted tale of realization and romance as both characters discover their true feelings for each other amidst comedic and heartfelt moments.

Sandra Bullock stars as Lucy, a dedicated environmental lawyer who ends up working for George, a carefree billionaire played by Hugh Grant. Their professional relationship takes a turn when Lucy decides she’s had enough of George’s antics and hands in her two-week notice.

This film uniquely combines comedy, romance, and personal growth, making it a standout choice for viewers searching for a lighthearted yet meaningful movie experience.

Two Weeks Notice (2002)

The Proposal (2009)

Movie NameThe Proposal (2009)
DirectorAnne Fletcher
ProducerDavid Hoberman
Release DateJune 1, 2009
Total Budget$40 million
Gross Profit$317.4 million

“The Proposal” is a 2009 romantic comedy that turns the classic love story on its head with witty and unexpected plot twists. Sandra Bullock shines as Margaret, a high-powered book editor from Canada, faces deportation due to an expired visa. In a bold move, she declares she’s engaged to her unsuspecting assistant, Andrew, played by Ryan Reynolds, who agrees to the charade under certain conditions. 

The movie is set in Alaska and weaves a hilarious narrative as the duo navigates their fake engagement in front of Andrew’s family. What starts as a business arrangement slowly changes into genuine affection, leading to laugh-out-loud moments and touching scenes. 

Moreover, “The Proposal” masterfully blends humor with heart, making it an irresistible watch for fans of romantic comedies seeking a story about unexpected love blossoming in the most unusual circumstances. 

The Proposal (2009)

How To Lose A Guy In 10 Days Plot

Dive into the captivating storyline of “How To Lose A Guy In 10 Days,” a romantic comedy that blends humor with the unpredictability of love. This engaging film follows Andie Anderson, a talented journalist who embarks on a unique assignment: to start dating a man and then drive him away within ten days using classic relationship mistakes.

Meanwhile, Benjamin Barry, an ambitious advertising executive, accepts the challenge of making a woman fall in love with him within the same timeframe. Their paths cross, leading to a short life of comedic situations and unexpected romance.

In addition, as they navigate their respective missions, both Andie and Ben find themselves tangled in a web of emotions, questioning their true feelings amidst their deceptive games. This lighthearted plot, filled with laughter and twists, showcases the unpredictable nature of love and the lessons it brings.

Box Office Collection

United States$105.8 million
Other countries$71.6
Box office budget$177.5 million


Concluding our blog on movies like How to Lose a Guy in 10 Days, let’s delve into the unique plot of this classic romantic comedy. The film presents a captivating cat-and-mouse game between Andie, a journalist played by Kate Hudson, and Ben, an advertising executive portrayed by Matthew McConaughey. Each film, with its unique twist on love and laughter, offers a fresh take on the quest for romance amidst comedic chaos.

From unexpected love pacts to hilarious dating blunders, these movies capture the essence of heartwarming and humorous connections. This clever setup leads to misadventures and comedic scenarios where both characters are entangled in their deceptions. After visiting the top choices mentioned above, you will have similar movies to watch if you like How to Lose a Guy in 10 Days.

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Jordan Counsel

Jordan Counsel is a passionate movie enthusiast with a keen eye for cinematic details. With years of experience in the film world, Jordan brings a unique perspective to the art of movie analysis and critique. Whether dissecting the latest blockbuster or delving into the nuances of independent cinema, Jordan's writing provides readers with insightful and engaging content. When not glued to the silver screen, Jordan enjoys exploring the world of cinema, attending film festivals, and sharing recommendations for movie lovers everywhere.