‘How to Lose a Guy in 10 Days’ Made the Unethical Wildly Romantic

All’s fair in love and war.

20 years ago today, How to Lose a Guy in 10 Days showed us how entertaining it can be to watch two terrible people fall in love. This beloved romantic comedy stars Kate Hudson and Matthew McConaughey. They play Andie and Ben, two attractive-yet-unlikable singles who manipulate and play mind games with each other over a period of ten days, accidentally falling in love in the process over the course of a remarkably entertaining story.

What Is ‘How to Lose a Guy in 10 Days’ About?

Kate Hudson as Andie and Matthew McConaughey Ben from How To Lose A Guy In 10 Days looking at each other
Image via Paramount Pictures

How to Lose a Guy in 10 Days follows Andie Anderson (Kate Hudson), a writer with her own advice column in the popular women’s magazine Composure. Tired of being limited to fashion and relationship advice, Andie longs to be taken seriously as a journalist and write about more serious topics like politics and international affairs. When her friend and co-worker Michelle (Kathryn Hahn) gets dumped after saying “I love you” just ten days in to a new relationship, Andie pitches a story wherein she will date a man and attempt to drive him away in ten days by committing all the dating faux pas women typically make in relationships. Her boss accepts the pitch, and even promises Andie to let her write about whatever she wants should the article be a success.


Andie’s experiment doesn’t quite go as planned because the man she sets her sights on is Benjamin Barry (Matthew McConaughey), an advertising executive who makes a bet that he can make any woman fall in love with him in 10 days. Looking to expand his horizons from the beer and sports ad campaigns he typically helms, Ben takes aim at an ad campaign for a large diamond company. His rivals Judy Spears (Michael Michele) and Judy Green (Shalom Harlow), who got word of Andie’s experiment after visiting Composure earlier that day, select Andie as the woman Ben must try to enamor in an attempt to sabotage him and secure the campaign for themselves.

Why ‘How to Lose a Guy in 10 Days’ Works

Andie and Ben’s contradictory intentions lead to a series of hijinks during which Andie becomes a caricature of a woman desperate for a boyfriend while Ben attempts to woo her. Andie is clingy, obsessive, and overly emotional, while Ben is suave, romantic, and amenable. Andie tries her best to drive Ben crazy and break up with her, but he refuses to back down and continues to put up with her increasingly unhinged behavior. But things become complicated when Andie and Ben start to develop real feelings for each other. They bond over their shared love for the New York Knicks, and in the moments where they drop the act and actually get to know each other, discover how compatible they are. When Ben takes Andie to meet his family, who receive her with open arms, she realizes she may be in over her head, and Ben wonders if it may be possible for him to walk away with Andie and the diamond campaign once the ten days are up.

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Andie and Ben’s objectives may be unethical, but How to Lose a Guy in 10 Days is grounded in a sense of lightheartedness that make their questionable actions easy to look past, due in no small part to the chemistry between actors Kate Hudson and Matthew McConaughey. There is a certain aspirational quality to the film as a whole – two young, wealthy New Yorkers who look like Abercrombie and Fitch models taking each other on expensive dates, culminating in a lavish ball thrown by a diamond company. This makes the final reveal a bit more palatable. Andie and Ben have both been using each other for their own personal gain, making the deception seem less sinister than other romantic comedies with similar premises like 10 Things I Hate About You or She’s All That, where only the woman is on the receiving end of the betrayal.

The now iconic scene where Andie sabotages Ben’s speech and forces an impromptu duet performance of Carly Simon’s “You’re So Vain” encapsulates all the good and the bad in their tumultuous relationship. Now that all the cards are on the table, they publicly embarrass themselves in an attempt to get back at the other. The song choice is particularly appropriate, as their vanity is what got them in the situation in the first place. How to Lose a Guy in 10 Days proves that sometimes watching hot people mess with each other’s heads is all you really need from a good rom-com.

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