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100+ Movies like How to Lose a Guy in 10 Days

3.4
2003 Comedy, Romance

Discover movies similar to the romantic comedy "How to Lose a Guy in 10 Days", where a writer sets out to drive away a man she's dating as part of an article assignment, while he tries to make her fall in love with him as part of a bet. Explore films featuring deceptive dating games, clashing romantic agendas, and the blurring lines between pretense and genuine feelings. Find stories of unlikely couples brought together by schemes and ulterior motives, navigating the complexities of modern relationships with humor and heart.

The Break-up Artist

The Break-up Artist

2.3
2009

Both "The Break-up Artist" and "How to Lose a Guy in 10 Days" revolve around a central premise of a woman setting out to intentionally sabotage a romantic relationship, only to unexpectedly fall for the man herself. In "The Break-up Artist", Britney's job is to break up couples, but she ends up in a relationship with Rick, her business rival, before plotting to ruin his company. Similarly in "How to Lose a Guy in 10 Days", Andie writes an article where she aims to drive a man away through obnoxious behavior, but develops genuine feelings for Ben. The movies share a parallel storyline of the female protagonist initially pursuing a deceptive agenda in the relationship, only to have her plans backfire as she grows closer to the man. This leads to a climactic reveal where the truth comes out and the couple must reconcile their feelings. Both films explore themes of love triumphing over manipulation and finding an authentic connection. The male leads, Rick and Ben, are positioned as the targets of the women's schemes before the dynamic shifts. Supporting characters like Ashley, Mike, and the friends assist or complicate the central romantic plot. Overall, the core narrative structure follows a similar progression of deception, a blossoming connection, a dramatic conflict, and an eventual romantic resolution.

Love & Sex

Love & Sex

3.1
2000

Both "Love & Sex" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy plot where the main female character embarks on a mission involving dating and relationships, initially with ulterior motives. In "Love & Sex", Kate is tasked with writing an article on loving relationships, while in "How to Lose a Guy in 10 Days", Andie aims to write an article by intentionally driving away a man she's dating. The protagonists meet their love interests, Ben and Adam, under pretenses and begin relationships with hidden agendas. However, genuine feelings develop despite their initial intentions. The relationships go through ups and downs, breakups, and reconciliations as the characters navigate the complexities of love and timing. Ultimately, the protagonists realize their true feelings and reunite with their love interests after overcoming misunderstandings and personal growth.

Beauty & the Briefcase

Beauty & the Briefcase

3.0
2010

Both "Beauty & the Briefcase" and "How to Lose a Guy in 10 Days" revolve around a woman working for a magazine who is assigned to write an article involving dating and relationships. They go undercover in a professional setting to find a romantic partner, initially with ulterior motives but eventually developing genuine feelings. The protagonists deceive their love interests about their true intentions, leading to conflict when the truth is revealed. However, the couples reconcile in the end after realizing their love for each other. The movies explore themes of self-discovery, the balance between career and romance, and the challenges of modern dating.

Top Five

Top Five

3.0
2014

Both "Top Five" and "How to Lose a Guy in 10 Days" follow a similar plot structure where the main characters are initially pursuing ulterior motives in their romantic relationships, unbeknownst to their partners. In Top Five, Chelsea is secretly a film critic tasked with interviewing Andre, while in How to Lose a Guy in 10 Days, Andie aims to drive Ben away for an article, and Ben aims to make Andie fall in love with him for a bet. As the stories progress, the characters develop genuine feelings for each other despite their initial deceptions. The relationships face major conflicts when the truth about their motives is revealed, leading to a breakup. However, the characters ultimately reconcile after realizing their true love for one another. Both films explore themes of honesty, trust, and the challenges of balancing career ambitions with romantic relationships.

Date Movie

Date Movie

2.1
2006

Both "Date Movie" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy plot where the main characters initially pursue a relationship under false pretenses, with one character trying to win over the other as part of a bet or challenge. The female lead pretends to act in an exaggerated, off-putting manner to drive the male lead away, while the male lead tries to make the female lead fall for him within a set timeframe. Despite their contrived motives, the characters develop genuine feelings for each other. Their deceptions are eventually revealed, leading to a breakup, but they reconcile after realizing their true love. The movies parallel each other in the core premise of feigned romantic pursuits turning into real connections, as well as the narrative arcs of initial attraction, growing affection, conflict due to revealed deceptions, and ultimate reconciliation.

Wedding Daze

Wedding Daze

2.8
2006

Both "Wedding Daze" and "How to Lose a Guy in 10 Days" revolve around a central romantic plot involving deception and ulterior motives. The protagonists, Andie and Anderson, embark on relationships under false pretenses - Andie aims to drive her partner away for an article, while Anderson proposes to a stranger on a whim. Their partners, Ben and Katie, are initially unaware of the true intentions behind the relationships. As the stories progress, genuine feelings develop between the couples despite the initial deceptions. The movies explore themes of love, honesty, and the complexities of modern relationships through comedic situations and misunderstandings. Ultimately, the couples reconcile and commit to their relationships after overcoming the initial obstacles and revelations about their ulterior motives.

On the Line

On the Line

2.4
2001

Both "On the Line" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy premise where the main characters embark on a quest related to pursuing or sabotaging a romantic relationship, unbeknownst to each other. In "On the Line", Kevin publicly searches for a woman he met briefly, while in "How to Lose a Guy in 10 Days", Andie tries to drive away a man she starts dating as part of an article experiment. The movies parallel each other as the characters' true intentions are hidden from their romantic interests, leading to misunderstandings and complications in their budding relationships. Ultimately, the characters overcome the deceptions and reveal their genuine feelings for each other. The movies share common themes of the challenges of modern dating, the power of public gestures in romance, and the importance of being true to oneself in relationships.

Friends with Benefits

Friends with Benefits

3.3
2011

Both "Friends with Benefits" and "How to Lose a Guy in 10 Days" revolve around a central premise of two people entering into a casual, no-strings-attached sexual relationship while pursuing ulterior motives related to their careers. In "Friends with Benefits," Jamie recruits Dylan for a job to earn a commission, while in "How to Lose a Guy in 10 Days," Andie aims to write an article by driving a man away, and Ben tries to make a woman fall for him for a work opportunity. Despite their initial intentions, the main characters develop genuine feelings for each other over time. The movies explore the complications of mixing romance and casual sex, as well as the challenges of balancing career ambitions with personal relationships. Both feature a climactic scene where the truth about their motives is revealed, leading to a temporary breakup before the characters reconcile and embrace their love.

Trainwreck

Trainwreck

2.9
2015

Both "Trainwreck" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy plot where the main characters initially pursue a relationship under false pretenses or ulterior motives, only to genuinely fall for each other. In Trainwreck, Amy sets out to write an article by dating Aaron with the intention of driving him away, while in How to Lose a Guy in 10 Days, Ben bets he can make any woman fall for him and chooses Andie. Despite their initial deceptions, Amy and Ben develop real feelings for their respective partners, Aaron and Andie. The movies explore themes of commitment issues, overcoming emotional barriers, and finding genuine love. The protagonists go through character arcs of self-discovery and growth, ultimately choosing to be vulnerable and pursue a meaningful relationship. Key story beats include the initial meeting, the gradual development of feelings, a major conflict or revelation of the deception, a breakup, and a grand romantic gesture to reconcile. Both films employ comedic elements and supporting characters to drive the narrative forward.

Set It Up

Set It Up

3.5
2018

Both "Set It Up" and "How to Lose a Guy in 10 Days" involve a central plot where two people pretend to be in a relationship for ulterior motives, only to develop genuine feelings for each other. In the "Set It Up", two assistants set up their bosses on dates to get them to stop overworking them, while in the "How to Lose a Guy in 10 Days", a woman tries to drive a man away as part of an article while he tries to make her fall for him on a bet. The movies follow the characters' schemes to manipulate the relationships, the growing romantic connections despite their intentions, the reveal of the deceptions, and the eventual reconciliation as the characters admit their true feelings. The movies explore themes of love versus deception, the challenges of modern dating, and finding fulfillment in work and relationships.

Hitch

Hitch

3.3
2005

Both "Hitch" and "How to Lose a Guy in 10 Days" revolve around a central premise of deception in the pursuit of romance. In "Hitch", the protagonist Alex Hitchens secretly works as a dating coach while concealing his true profession from the woman he falls for, Sara. Similarly, in "How to Lose a Guy in 10 Days", Andie Anderson and Benjamin Barry engage in deceptive bets related to their dating lives without revealing their ulterior motives to each other. The movies explore the complications and consequences that arise when the characters' true intentions are eventually exposed, threatening their budding relationships. The protagonists in both films initially approach romance from a cynical or calculated perspective - Hitch as a professional dating consultant and Andie through her article's premise of intentionally sabotaging a relationship. However, they unexpectedly develop genuine feelings for their respective love interests, leading to internal conflicts between their professional/personal goals and their emotional desires. This parallel journey of transitioning from a detached, strategic mindset to an authentic emotional connection is a central theme shared by the two stories. Both movies also feature subplots involving the protagonists' friends or clients navigating their own romantic entanglements, which intersect with and mirror the main storylines. These secondary relationships serve as counterpoints or foils to the central romances, highlighting the contrasts between genuine emotional connections and more superficial or manipulative pursuits.

Love Tactics

Love Tactics

3.6
2022

Both "Love Tactics" and "How to Lose a Guy in 10 Days" follow a similar premise of two people entering into a bet or challenge to make someone fall in love with them, unbeknownst to their targets. The protagonists, Aslı and Andie, accept challenges to make a man fall for them using tactics and manipulative behavior, while the men, Kerem and Ben, accept bets to make a woman fall in love with them within a set timeframe. The movies explore the dynamics of these challenges, with the protagonists initially pursuing their goals through deception but eventually developing genuine feelings for each other. The challenges lead to a series of humorous and romantic situations as the characters employ various tactics to achieve their objectives. However, the truth about the bets and challenges is eventually revealed, causing conflict and a temporary breakup. In the end, the protagonists reconcile and confess their true feelings, overcoming the initial deception and finding genuine love.

Love Again

Love Again

3.3
2023

Both "Love Again" and "How to Lose a Guy in 10 Days" revolve around a central romantic plot where the main characters initially pursue a relationship under false pretenses or ulterior motives, only to genuinely fall for each other over time. In "Love Again", Rob begins texting Mira anonymously while assigned to write about Celine Dion, while in "How to Lose a Guy in 10 Days", Andie dates Ben as part of an article experiment to drive him away. Despite their deceptions, Rob and Ben both end up developing real feelings for Mira and Andie respectively. The movies also share similar themes of overcoming cynicism about love, the transformative power of romance, and the importance of being honest in relationships. Key plot points include the protagonists bonding over shared interests and experiences, meeting each other's families, and a climactic confrontation where the truth is revealed, leading to a temporary breakup before the couples ultimately reconcile.

Knocked Up

Knocked Up

3.1
2007

Both "Knocked Up" and "How to Lose a Guy in 10 Days" revolve around an unexpected pregnancy resulting from a one-night stand between two people with vastly different lifestyles and personalities. The main characters initially have nothing in common and go their separate ways after the casual encounter, only to be brought back together by the pregnancy. They then embark on an unlikely relationship, facing challenges and doubts along the way as they navigate their contrasting values and priorities. The stories follow their personal growth and the evolution of their relationship as they come to terms with becoming parents together. Ultimately, they overcome their differences and commit to raising the child as a couple, marking a significant turning point in their lives.

The Baxter

The Baxter

3.1
2005

Both "The Baxter" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy plot where the main characters initially pursue a relationship under false pretenses or ulterior motives, only to genuinely fall for each other over time. In "The Baxter", Elliot tries to avoid being the stereotypical "nice guy" who loses the girl, while in "How to Lose a Guy in 10 Days", Andie aims to drive a man away through stereotypical needy behavior. Meanwhile, Ben in the latter movie bets he can make any woman fall for him. As Elliot and Andie spend time with their respective love interests Cecil and Ben, they develop real feelings despite their initial intentions. The movies parallel each other in the protagonists' journeys from cynical, calculated approaches to romance to genuine emotional connections. Key plot points like the protagonists' friends learning about the deceptions, and climactic confrontations where the truth comes out, further highlight the structural similarities between the two romantic comedy stories.

Love Hard

Love Hard

3.5
2021

Both "Love Hard" and "How to Lose a Guy in 10 Days" revolve around a central deception involving dating and relationships. In "Love Hard", Natalie is catfished by Josh using another man's pictures, while in "How to Lose a Guy in 10 Days", Andie and Ben engage in a bet where they deceive each other about their true intentions. The protagonists in both films initially pursue a romantic interest under false pretenses, only to develop genuine feelings over time. This leads to a climactic reveal of the deception and a conflict that must be resolved. Ultimately, the main characters find their way back to each other after being honest about their feelings. The movies explore themes of honesty, self-acceptance, and the complexities of modern dating through a comedic lens.

Isn't It Romantic

Isn't It Romantic

3.1
2019

Both "Isn't It Romantic" and "How to Lose a Guy in 10 Days" follow a similar romantic comedy plot where the female protagonist initially dislikes or is cynical about romantic relationships, but ends up falling for a man despite her initial intentions. In "Isn't It Romantic", Natalie hates romantic comedies but finds herself trapped in one, while in "How to Lose a Guy in 10 Days", Andie sets out to drive a man away but ends up falling for him. The protagonists' journeys involve overcoming their own insecurities and learning to embrace love and romance. There is also a bet or challenge involved, with Natalie needing to find true love to escape the romantic comedy world, and Ben needing to make Andie fall for him to win a work opportunity. Both movies feature a love triangle with another romantic interest besides the main love interest. The stories culminate in the protagonists realizing their true feelings and embracing a romantic relationship.

The Ugly Truth

The Ugly Truth

3.2
2009

Both "The Ugly Truth" and "How to Lose a Guy in 10 Days" follow a similar plot structure where a cynical, commitment-phobic man is tasked with making a romantic woman fall in love with him, while the woman has her own ulterior motive to drive him away. In both cases, the man uses manipulative tactics to win over the woman, but ends up genuinely falling for her. The woman initially plays along with the man's games, but eventually realizes her true feelings for him. There is a conflict when the truth about their deceptions comes out, leading to a breakup, but they ultimately reconcile after realizing their love is genuine. The movies explore themes of love versus manipulation, the battle of the sexes, and finding true compatibility beyond superficial games.

Celeste & Jesse Forever

Celeste & Jesse Forever

3.2
2012

Both "Celeste & Jesse Forever" and "How to Lose a Guy in 10 Days" center around a romantic relationship between the main characters that goes through ups and downs, with the couple separating or divorcing but maintaining an unconventional closeness that confuses their friends. The female lead initially wants to end the relationship but later has a change of heart and tries to reconcile, while the male lead moves on to a new romantic interest. There are misunderstandings and deceptions around the true intentions of the characters. The movies explore themes of love, commitment, and the difficulties of moving on from a past relationship. Ultimately, the main characters realize their enduring feelings for each other and rekindle their romance after overcoming obstacles and personal growth.

Kissing Jessica Stein

Kissing Jessica Stein

3.0
2002

Both "Kissing Jessica Stein" and "How to Lose a Guy in 10 Days" revolve around a woman who embarks on an unconventional romantic relationship as part of an ulterior motive or experiment, only to unexpectedly develop genuine feelings for her partner. In "Kissing Jessica Stein," Jessica responds to a personal ad from Helen seeking a same-sex relationship, initially as a curious experiment but grows to care for Helen. Similarly in "How to Lose a Guy in 10 Days," Andie pursues a relationship with Ben as part of an article premise to drive him away, but she falls for him instead. The women's ulterior motives create tension and conflict when their true intentions are revealed to their partners, nearly derailing the relationships. However, the couples reconcile after realizing their authentic connection. Both films explore themes of overcoming preconceptions, embracing one's true self, and the complexities of modern dating and relationships. The narratives follow a similar arc of initial deception, developing intimacy, a dramatic conflict, and ultimately finding acceptance and happiness together.