How to Lose a Guy in 10 Days

Andie Anderson and Benjamin Barry enter a New York City office with ten days to complete opposite bets. Andie, an advice columnist for Women's Daily, must convince a client she can make any man fall out of love in under two weeks. Benjamin, a high-stakes advertising executive, has wagered he can woo the woman who hates him most within that same window.

Their paths cross at a charity gala, sparking an immediate clash of wits and wills. What begins as a strategic game of manipulation quickly spirals into a chaotic dance of deception. Both characters find themselves trapped in a web of their own making as they attempt to sabotage or secure a relationship that never stood a chance of being real. [edit]

Andie Anderson works as a struggling advice columnist for Women's Daily, a prominent New York City women's magazine. Her career faces a critical turning point when her editor, Lana Jong, assigns her a high-stakes challenge: write a column detailing how to make any man fall out of love in just ten days. To prove the column's validity and save her job, Andie must personally execute the plan on a real man. She accepts the bet with confidence despite having no prior experience in romantic sabotage.

Simultaneously, Benjamin Barry operates at the top of his game as a charismatic advertising executive known for his womanizing ways and ability to close multi-million dollar deals. His personal life remains equally transactional. Ben makes a wager with his colleagues that he can make any woman fall in love with him within ten days. His target is specifically Andie Anderson, whom he finds irritatingly blunt and difficult to woo. He views her as the ultimate test of his skills.

The two meet at a charity gala where their paths cross amidst a clash of personalities. Andie immediately identifies Ben as the perfect subject for her column, while Ben sees Andie as the perfect conquest for his bet. They begin a whirlwind courtship that is less about genuine connection and more about strategic maneuvering. As the ten days progress, Andie employs a barrage of annoying tactics designed to drive men away. She talks about her ex-boyfriend constantly, wears ridiculous outfits, becomes overly clingy, and feigns an obsession with pets. She even hires a stalker to scare him off.

Conversely, Ben counters every one of her attempts by playing the role of the perfect, patient, and understanding boyfriend. He tolerates her eccentricities, supports her career ambitions, and seemingly adapts to her worst behavior, which only deepens Andie's confusion. The line between performance and reality begins to blur as the days tick by. Andie starts to notice that Ben's patience isn't just a tactic; there are moments of genuine kindness and understanding that surprise her. Meanwhile, Ben finds himself genuinely drawn to Andie's wit and independence, qualities he usually dislikes.

The central conflict intensifies as both characters struggle with the ethical implications of their bets. Andie faces pressure from her magazine to deliver a sensational story, while Ben risks his professional reputation if he fails to win over the woman who hates him most. Their relationship evolves into a complex dance of manipulation and vulnerability. Comedic set pieces involve basketball games, awkward family dinners, and public misunderstandings. Tension reaches a peak as the deadline approaches. Both characters are now deeply entangled in a web of lies, unsure of whether their feelings are real or part of the game. Andie begins to question if she actually wants to lose Ben, while Ben struggles with the realization that winning the bet might mean losing the one person who truly challenges him. The story builds toward a climax where the truth of their intentions must be revealed, threatening to shatter the fragile connection they have built. As the final day arrives, both must decide whether to walk away from the game or risk everything for a chance at something real.[edit]