Movies Similar to How to Lose a Guy in 10 Days Unleashed

If you watch movies for the sake of romance and love themes, then movies similar to How to Lose a Guy in 10 Days will be worthwhile for you. The film reflects the funny interaction between a lady who is the columnist who wants to lose a guy and a boy who is looking for a date with her. The combination of these two contrary happenings creates a humor and romantic journey.

Here starts the romantic campaign of lovely stories that amuse the viewers through lighthearted fun and love. Some of these movies recall the classical glimpses of previous work, whereas some are the latest superhit releases. In this article, we have shared several films’ detailed descriptions and plots.

Similar Movies to How to Lose a Guy in 10 Days (2003)

Twenty romantic and laughter-arousing films are described below that will entertain you throughout the movies. A table of information is also included in the movie’s description. 

The Princess Diaries (2001)

Film Name (Year)The Princess Diaries (2001)
Box Office Return$165.3 million
Filmmaking Expense$26 million
DirectorGarry Marshall
ProducerWhitney Houston
Running Time115 minutes
Release DateJuly 29, 2001

The Princess Diaries (2001) is a lighthearted comedy film allowing viewers to enjoy the family content. The movie begins with a plot where Mia Thermopolis, a reserved teen from San Francisco, is shocked to discover that she is actually royalty.

Unexpectedly, she learns she is the successor to the throne of the tiny European nation of Genovia. Her path to becoming a princess is filled with humor and challenges, especially when her stern and imposing grandmother, Queen Clarisse, arrives to provide her with “princess lessons” for excellence. The Princess Diaries (2001) like films, are a treasure of romance-type movies.

About the Princess Diaries (2001)

White Chicks (2004)

Film Name (Year)White Chicks (2004)
Box Office Return$113.1 million
Filmmaking Expense$37 million
DirectorKeenen Ivory Wayans
ProducerKeenen Ivory Wayans
Running Time109 minutes
Release DateJune 23, 2004

White Chicks (2004) film is a blend of comedy and crime story directed by Keenen Ivory. Brothers Marcus and Kevin, both FBI agents, mismanage a major drug sting. As a consequence, they are assigned to chaperone two socialites (Rochelle Aytes Anne Dudek) to the Hamptons as part of a scheme to trap a kidnapper. 

However, the socialites hesitated about the plan and refused to participate. Desperate, Marcus and Kevin cover themselves as the sisters, undergoing a complete transformation from African-American men into blonde, white women. For complete amusement, romantic comedies like White Chicks films reflect the fun.

About White Chicks (2004)

Bring It On (2000)

Film Name (Year)Bring It On (2000)
Box Office Return$90.5 million
Filmmaking Expense$11 million
DirectorPeyton Reed
ProducerMarc Abraham
Running Time99 minutes
Release DateAugust 25, 2000

Bring It On (2000) combines comedy and romance, providing viewers with complete entertainment. The cheerleading team at Rancho Carne High School in San Diego, the Toros, is bursting with energy, attitude, and a stunning routine, poised to secure their sixth consecutive national championship.

However, for the freshly appointed captain, Torrance, the path to ultimate cheerleading victory turns uncertain when she uncovers that their flawless routines were actually imitative from the Clovers, a dynamic hip-hop team from East Compton, by the previous Toro captain and his team. Bring It On (2000) like stories, entertain the lighthearted comedy lovers with romance.

About Bring It On (2000) 

Mean Girls (2004)

Film Name (Year)Mean Girls (2004)
Box Office Return$130.1 million
Filmmaking Expense$18 million
DirectorMark Waters
ProducerLorne Michaels
Running Time97 minutes
Release DateApril 19, 2004

Mean Girls (2004) is a film about young adults who perform different roles that arouse fun and romanticism. Young Cady Heron, who was homeschooled in Africa by her scientist parents, relocates with her family to residential land. 

Here, Cady attends public school for the first time and quickly learns about the harsh, unspoken rules of popularity that segregate her peers into rigid cliques. Unexpectedly, she is accepted by an exclusive group known as “the Plastics,” but it doesn’t take long for Cady to understand why her new friends have such a superficial reputation. Unveiling romantic collections like Mean Girls are pretty amusing for love fiction buffs.

Mean Girls (2004)

When Harry Met Sally (1989)

Film Name (Year)When Harry Met Sally (1989)
Box Office Return$92.8 million
Filmmaking Expense$16 million
DirectorRob Reiner
ProducerRob Reiner
Running Time96 minutes
Release DateJuly 14, 1989

When Harry Met Sally (1989) is a romantic film that includes comedy and fun. The plot unveils fresh college graduates Harry Burns and Sally Albright, who endure a car ride from Chicago to New York in 1977. Debating if men and women can ever be just friends. 

A decade later, they bump into each other at a bookstore and, along with their best friends Jess and Marie, try to maintain a friendship without letting romance complicate things. Unveiling romantic movies like When Harry Met Sally will be a fascinating experience for movie lovers.

When Harry Met Sally (1989)

Two Weeks Notice (2002)

Film Name (Year)Two Weeks Notice (2002)
Box Office Return$199 million
Filmmaking Expense$60 million
DirectorMarc Lawrence
ProducerSandra Bullock
Running Time102 minutes
Release DateDecember 20, 2002

Two Weeks Notice (2002) film is a reflection of lightweight comedy in the form of dramatic presentation. The story begins when passionate environmental lawyer Lucy Kelson joins billionaire George Wade in a deal aimed at saving a community center. 

Over time, George becomes dependent on Lucy for advice on everything from legal issues to fashion choices. Frustrated by his dependency, Lucy resigns and selects Harvard graduate June Carter to take her place. When her departure from the firm approaches, Lucy begins to feel jealous of June and starts to reconsider her decision to leave George due to the reason.

Two Weeks Notice (2002)

The Proposal (2009)

Film Name (Year)The Proposal (2009)
Box Office Return$317.4 million
Filmmaking Expense$40 million
DirectorAnne Fletcher
ProducerDavid Hoberman
Running Time108 minutes
Release DateJune 1, 2009

The Proposal (2009) is a hub of comedy and romance where entertainment is the source of joyfulness. By avoiding deportation to Canada, a formidable book editor-in-chief Margaret Tate claims she is engaged to her unsuspecting assistant, Andrew Paxton. 

Andrew consents to the trick but sets his own terms, including a trip to Alaska to meet his family. With a doubtful immigration officer constantly on their trail, Margaret and Andrew must adhere to their wedding scheme, navigating various comedic obstacles.

The Proposal (2009)

The Holiday (2006)

Film Name (Year)The Holiday (2006)
Box Office Return$205.8 million
Filmmaking Expense$85 million
DirectorNancy Meyers
ProducerNancy Meyers
Running Time136 minutes
Release DateNovember 29, 2006

The Holiday (2006) is a lovely comedy movie that entertains you through funny dialogues and fun. The movie plots unveil the heartbroken and hopeless Englishwoman Iris, who decides to exchange homes with Amanda, a Californian who has also had no luck in love, seeking a refreshing change of scenery. 

Iris ends up in a luxurious Hollywood estate, while Amanda adjusts to the pretty charm of a picturesque English village. Before long, both women encountered local men who seemed ideal for a romantic rebound. The Holiday (2006) is one of the movies similar to How to Lose a Guy in 10 Days.

The Holiday (2006)

Legally Blonde (2001)

Film Name (Year)Legally Blonde (2001)
Box Office Return$141.8 million
Filmmaking Expense$18 million
DirectorRobert Luketic
ProducerMarc Platt
Running Time96 minutes
Release DateJuly 13, 2001

Legally Blonde (2001) is a romantic fiction and humorous film about the delightful experience of a lady. The movie is about Elle Woods, who seemingly has everything she could desire and dreams of becoming Mrs. Warner Huntington III.

However, Warner hesitates to propose because he thinks she is too blonde. Undeterred, Elle marshals all her efforts to gain admission to Harvard, resolute in her mission to win him back again with some efforts. If you want to enjoy more movies similar to How to Lose a Guy in 10 Days, then watch Legally Blonde (2001). 

Legally Blonde (2001)

The Devil Wears Prada (2006)

Film Name (Year)The Devil Wears Prada (2006)
Box Office Return$326.7 million
Filmmaking Expense$35–41 million
DirectorDavid Frankel
ProducerWendy Finerman
Running Time109 minutes
Release DateJune 22, 2006

The Devil Wears Prada (2006) film is a fine combination of comedy and musical composition filmized under the direction of David Frankel. Andy, a recent college former student with ambitious aspirations, secures a position at the renowned Runway magazine. She becomes the assistant to the authoritarian editor, Miranda Priestly. 

Andy doubts her capacity to endure the exhausting tenure as Miranda’s struggling assistant without getting burned out. This amazing movie will let you enjoy similar taste as the movies similar to How to Lose a Guy in 10 Days.

The Devil Wears Prada (2006)

13 Going on 30 (2004)

Film Name (Year)13 Going on 30 (2004)
Box Office Return$96.5 million
Filmmaking Expense$37 million
DirectorGary Winick
ProducerSusan Arnold
Running Time98 minutes
Release DateApril 23, 2004

13 Going on 30 (2004) film is a beautiful reflection of fantasies and romance, allowing viewers to enjoy the entertainment with easy steps. The movie starts when a young girl who is fed up with various restrictions at school turns into an adult overnight. 

In this heartwarming fairy tale, teenager Jenna longs for a boyfriend but, frustrated by her inability to find one, dreams of being a confident adult. Miraculously, her wish comes true, and she wakes up as a 30-year-old Jennifer. However, she soon discovers that adulthood, with its own complex relationship issues, is far from simple.

13 Going on 30 (2004)

Grown Ups (2010)

Film Name (Year)Grown Ups (2010)
Box Office Return$272.2 million
Filmmaking Expense$75 million
DirectorDennis Dugan
ProducerAdam Sandler
Running Time102 minutes
Release DateJune 25, 2010

Grown Ups (2010) is a comedy plus drama film that provides ongoing plot depiction through interesting story-telling. The movie is about a man with a drinking problem. A father who seldom visits his three daughters. An unemployed, overweight individual. 

A househusband under his wife’s thumb. A thriving Hollywood agent married to a fashion designer. What ties these five men together? They were once teammates on their high school basketball team. Reunited at their former coach’s funeral, and their reunion will be challenging.

Grown Ups (2010)

Dodgeball: A True Underdog Story (2004)

Film Name (Year)Dodgeball: A True Underdog Story (2004)
Box Office Return$168.4 million
Filmmaking Expense$20 million
DirectorRawson Thurber
ProducerBen Stiller
Running Time92 minutes
Release DateJune 18, 2004

Dodgeball: A True Underdog Story (2004) is a comedy film based on the sports theme in which fun is an absolutely pivotal factor. The movie’s plot reveals the story of Joe and his owner, Peter, whose luck is not supporting them in most cases. Peter is facing the challenge of continuing the gym operationality by lacking the debt of $50,000.

To decrease their financial deficits, Peter and Joe’s average group arranged a contest with a significant cash prize, which was entitled “dodgeball.” Organizing the event aims to bring financial stability and promote the arena. The competition takes a hilarious turn when the contestants have funny encounters with the ball.

Dodgeball A True Underdog Story (2004)

Superbad (2007)

Film Name (Year)Superbad (2007)
Box Office Return$170.8 million
Filmmaking Expense$17.5–20 million
DirectorGreg Mottola
ProducerJudd Apatow
Running Time113 minutes
Release DateAugust 13, 2007

Superbad (2007) is a superhit comedy film portrayed by young characters to create unlimited laughter and amusement. The movie describes the story of two best buddies, inseparable as ever, nearing the end of their high school journey. Their excitement peaks as they receive invites to a massive house party. 

Determined to make it a memorable night, they enlist the help of their friend to convince alcohol and woo some ladies. However, their plans take an unexpected turn when one of them gets entangled with two unfortunate cops who have their agenda for the evening. If you are in search of more How to Lose a Guy in 10 Days similar movies, you should go for Superbad (2007) film.

Superbad (2007)

Crazy Rich Asians (2018)

Film Name (Year)Crazy Rich Asians (2018)
Box Office Return$239 million
Filmmaking Expense$30 million
DirectorJon M. Chu
ProducerNina Jacobson
Running Time121 minutes
Release DateAugust 7, 2018

Crazy Rich Asians (2018) film is created on a romantic theme with a comedy touch under the direction of Jon M. Chu. The film describes the story of Rachel Chu, who agrees to join Nick at a wedding in Singapore, dipping herself in a flurry of surprises. 

Unveiling Nick’s family’s vast fortune and his prominence as a desirable bachelor in the nation, Rachel is withdrawn. During this journey, she crosses paths with jealous high society members, unconventional relatives, and Nick’s doubtful mother, much to her action, casting shadows on their bond. In How to Lose a Guy in 10 Days, in movies similar to this story, romanticism is common, just like Crazy Rich Asians (2018).

Crazy Rich Asians (2018)

The Wolf of Wall Street (2013)

Film Name (Year)The Wolf of Wall Street (2013)
Box Office Return$406.9 million
Filmmaking Expense$100 million
DirectorMartin Scorsese
ProducerMartin Scorsese
Running Time180 minutes
Release DateDecember 17, 2013

The Wolf of Wall Street (2013) is one of the best comedy films that reflect romance and bonding. Martin Scorsese directed it. The plot tells the story of Jordan Belfort, who secured an entry-level position at a prestigious Wall Street brokerage house. 

Fast forward to the early 1990s, Belfort establishes his firm, Stratton Oakmont, while still in his twenties. Alongside his loyal right-hand man Jonah and a spirited team of brokers, Belfort collects enormous wealth by manipulating wealthy investors. However, as Belfort and his associates indulge in a wild lifestyle of dishonesty, law enforcement agencies such as the SEC and the FBI begin to close due to intense involvement. 

The Wolf of Wall Street (2013)

The Hangover (2009)

Film Name (Year)The Hangover (2009)
Box Office Return$469.3 million
Filmmaking Expense$35 million
DirectorTodd Phillips
ProducerTodd Phillips
Running Time100 minutes
Release DateMay 30, 2009

The Hangover (2009) is a dark comedy film that describes the story of a mysterious plot with a combination of fun. Following the chaos of Las Vegas, Stu prepares to tie the knot two years later. Opting for a wedding in Thailand due to his bride’s origin, Stu plans a seemingly tame pre-wedding brunch to sidestep the calamity of Doug’s bachelor party. 

However, with Phil and Alan back in the picture and considering the unpredictable nature of Thailand, Stu soon realizes that anything but a calm affair awaits him. Moreover, the movie set record success against its short-range budget with a giant return.

The Hangover (2009)

Anyone But You (2023)

Film Name (Year)Anyone But You (2023)
Box Office Return$219.6 million
Filmmaking Expense$25 million
DirectorWill Gluck
ProducerWill Gluck
Running Time103 minutes
Release DateDecember 11, 2023

Anyone But You (2023) is another romantic comedy filmized in America under the direction of Will Gluck. The movie describes the dating experience of a young couple whose interaction is pivotal in the story. 

Although their first date is promising, Bea and Ben’s first spark fizzles out soon after. Their journey takes an unexpected turn when they wind up at a destination marriage in Australia. In a bid to maintain appearances, they cover up as the ideal couple despite their underlying tension.

Anyone But You (2023)

Johnny English Reborn (2011)

Film Name (Year)Johnny English Reborn (2011)
Box Office Return$160.1 million
Filmmaking Expense$45 million
DirectorOliver Parker
ProducerTim Bevan
Running Time102 minutes
Release DateOctober 7, 2011

Johnny English Reborn (2011) is a complete comedy film full of action under the direction of Oliver Parker. Following a failed operation in Mozambique, British agent Johnny English seeks comfort in a Tibetan monastery, attempting to erase the memory of his embarrassment. 

However, his peace is short-lived when MI-7 urgently summons him for a mission tailored to his unique abilities. Armed with his unconventional combat tactics and an array of advanced gadgets, English teams up with his fresh ally, Agent Tucker, to frustrate an assassination scheme targeting the premiership.

Johnny English Reborn (2011)

Clueless (1995)

Film Name (Year)Clueless (1995)
Box Office Return$88 million
Filmmaking Expense$12 million
DirectorAmy Heckerling
ProducerScott Rudin
Running Time97 minutes
Release DateJuly 19, 1995

Clueless (1995) is a young characters-based comedy film directed by Amy Heckerling in America. At the successful point of Beverly Hills High School’s social hierarchy reigns Cher, who is wealthy, superficial, and adept at navigating social circles. She fancies herself a cupid, orchestrating a romance between two teachers as her first matchmaking venture. 

Sustained by this triumph, she sets out to transform the awkward new student, Tai. However, when Tai surpasses her in popularity, Cher acknowledges the wisdom of her critical ex-stepbrother Paul and finds herself drawn to him.

Clueless (1995)

About How to Lose a Guy in 10 Days (2003)

Film Name (Year)How to Lose a Guy in 10 Days (2003)
Box Office Return$177.5 million
Filmmaking Expense$50 million
DirectorDonald Petrie
ProducerLynda Obst
Running Time116 minutes
Release DateFebruary 7, 2003

How to Lose a Guy in 10 Days (2003) is based on a lighthearted comedy that includes romance and lovely story-telling. The movie reveals the story of Andie Anderson, an advice columnist who ventures into uncharted territory with her latest article on how to repel a man in 10 days.

Her editor, Lana, approves, prompting Andie to embark on a quest to find a suitable subject for her experiment. Enter administrative Ben Berry, full of confidence in his ability to win over any woman within the same timeframe. However, when Ben and Andie cross paths, their schemes take an unexpected turn.

About How to Lose a Guy in 10 Days (2003)

How to Lose a Guy in 10 Days (2003) Cast

  • Matthew McConaughey performed the role of Benjamin Barry.
  • Kate Hudson played the role of Andie Anderson.
  • Adam Goldberg appeared as Tony.
  • Michael Michele played the role of Judy Spears.
  • Shalom Harlow performed the character of Judy Green.
  • Kathryn Hahn worked as Michelle.
  • Thomas Lennon worked as Thayer.
  • Celia Weston appeared as Glenda.
  • Annie Parisse performed the character of Jeannie.

Box Office Performance 

How to Lose a Guy in 10 Days (2003)
USA and Canada$105.8 million
Other Territories$71.7 million
Overall Amount$177.5 million


Overall, the above-shared movies similar to How to Lose a Guy in 10 Days, are jam-packed entertainment sources that include comedy, fun, and romance. The movie appears as a perfect blend of contrary happenings in which a lady is more likely to avoid someone who is trying to approach her. 

The movie succeeded in achieving significance at the box office regarding revenue generation or public response. Based on the viewers’ interest, we have brought more rom-com films for complete amusement without any fee. So, have a look at the above stories by overviewing the plots before watching the live action on screens.

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Castro Silva

Castro Silva is a digital nomad with an insatiable curiosity for uncovering exceptional websites dedicated to movies, manga, and anime. As a regular contributor to online publications, he's known for spotting user-friendly web experiences and sharing his discoveries. With a Bachelor's degree in Digital Media Studies from Stanford University, he combines academic knowledge with ongoing self-education in web development and user experience design. Castro has become a trusted curator of websites that enhance movie, manga, and anime experiences.