Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign, bets that he can make a woman fall in love with him in 10 days.


Donald Petrie


Michele Alexander (book), Jeannie Long (book) | 3 more credits »
2,040 ( 517)
1 win & 8 nominations. See more awards »





Cast overview, first billed only:
Kate Hudson ... Andie
Matthew McConaughey ... Ben
Kathryn Hahn ... Michelle
Annie Parisse ... Jeannie
Adam Goldberg ... Tony
Thomas Lennon ... Thayer
Michael Michele ... Spears
Shalom Harlow ... Green
Robert Klein ... Phillip Warren
Bebe Neuwirth ... Lana Jong
Samantha Quan ... Lori
Justin Peroff Justin Peroff ... Mike
Celia Weston ... Glenda
James Murtaugh ... Jack
Archie MacGregor ... Uncle Arnold


Benjamin Barry is an advertising executive competing with two female co-workers for a major campaign for a diamond merchant. He cuts a deal with his competitors that the account is his if he can make a woman of their choice fall in love with him in 10 days. In comes Andie Anderson who, in turn, is writing a story on how to lose a guy in 10 days as a bet with her boss to be allowed to write more substantial stories. With a hidden agenda in each camp, will either party be able to complete their mission? Written by Peter Brandt Nielsen

Plot Summary | Add Synopsis


One of them is lying. So is the other.


Comedy | Romance

Motion Picture Rating (MPAA)

Rated PG-13 for some sex-related material | See all certifications »

Parents Guide:

View content advisory »

Did You Know?


The dress Andie wears to the Warren Advertising gala was designed around the 84-carat yellow diamond pendant which she wears at the gala. It was designed by fashion designer Dina Bar-El, not the film's costume designer Karen Patch. See more »


At the end when Andie and Ben are kissing, Andie is on the left. In the next shot, she is on the right. See more »


[first lines]
Jeannie Ashcroft: [reading] "And only then will the people of Tajikistan know true and lasting peace." Andie, it's brilliant. It's really moving. But it's never going to appear in Composure Magazine.
See more »


Who Do You Love
by Bo Diddley (as Ellas McDaniel)
Performed by George Thorogood & The Destroyers
Courtesy of Rounder Records
By Arrangement with Ocean Park Music Group
See more »

User Reviews

Damn Near Perfect
30 November 2019 | by michaeltrivediSee all my reviews

Matthew M. is best in romantic comedies. It's his best type of movie. He's not the most handsome guy, and a little on the random side. But for some reason he shines in these movies. Who knows?

This is some good stuff right here. Perhaps one of the best rom coms ever. The movie is about a man meeting a woman. The man is supposed to make a girl fall in love with him, while the woman is supposed to make the man fall out of love with her. She's a journalist doing it for a story, and he's doing it for work as well. They fall in love at the end.

It's a powerful vehicle. Both Hudson and M shine pretty bright. It has its dull moments, but comes together beautifully in the end. It's fun to see the relationship drama, and both trying to trick the other. Family gets involved too, mixed with career, it's a hit.

Watch it!

7 stars

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USA | Germany



Release Date:

7 February 2003 (USA) See more »

Also Known As:

How to Lose a Guy See more »


Box Office


$50,000,000 (estimated)

Opening Weekend USA:

$23,774,850, 9 February 2003

Gross USA:


Cumulative Worldwide Gross:

See more on IMDbPro »

Company Credits

Show more on IMDbPro »

Technical Specs


Sound Mix:

DTS | Dolby Digital | DTS (Digital DTS Sound)| SDDS



Aspect Ratio:

1.85 : 1
See full technical specs »

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