Based on a short cartoon book of the same name by Michele Alexander and Jeannie Long, this light RomanticComedy film was directed by Donald Petrie (of other [[ChickFlick chick flicks]] such as ''MissCongeniality'', and ''Film/MysticPizza''), won the 2003 BMI Film Music Award, and was nominated for several categories by the MTV Movie and Teen Choice Awards.
Benjamin Barry is an advertising executive and ladies' man who, to win a big campaign by a diamond syndicate, bets that he can make a woman fall in love with him in 10 days. Andie Anderson covers the "How To" beat for "Composure" magazine and is assigned to write an article on "How to Lose a Guy in 10 Days." They meet in a bar shortly after the bet is made and HilarityEnsues.
!The film contains examples of:
* AlliterativeName: Andie Anderson.
** Benjamin Barry too.
* BabyTalk: Andie uses this as one of the methods to make men run away fast.
* BasedOnAnAdviceBook: Well, actually a woman's magazine in this case.
* BestFriendManual: Ben's mother lets slip that Andie is the first girl Ben ever brought home. It's not exactly advice, but it's a "heads up" insight that let her see the context.
* TheBet: Andie makes one with her boss. Ben makes one with his boss. [[DoubleStandard Note that the woman is only doing it out of creative integrity, while the man is doing it just for money]].
** Interestingly her so-called "creative integrity" leads to her manipulating a guy because she originally sees him as nothing more than a means to get some creative freedom. Ben, by contrast, is just doing his best to be charming (which isn't outside the realm of normal dating) and not giving up on Andie, to win a lucrative account for his company. Basically, both of them have to learn to stop manipulating the other just to get what they want.
** Of course, Andie's boss then renegs on the deal, saying that Andie can write about anything she wants... as long as it's trivial. [[spoiler:Andie quits on the spot]].
* ChickFlick: Oh, Matthew, take that shirt off!
** In-universe, they attend a Chick Flick Marathon, consisting of ''Film/SleeplessInSeattle'', ''Film/FriedGreenTomatoes'', ''Film/MysticPizza'', and ''Film/WhenHarryMetSally''. Pretty sure this constitutes ColdBloodedTorture.
* DeathbringerTheAdorable: Krull, looking natty in his Burberry sweater!
* DefconFive: "I have to crack this guy. I mean, this is Defcon Five, and I have to do something truly appalling. It's not funny." Possibly makes sense in this context, however, as their situation is going rather well due to Ben doing everything in his power to not break up with her, while she's trying to make things worse until he does.
* EveryoneLovesBlondes: Andie Anderson is so gorgeous she 'could throw up on a guy and he'd say, “Do it again.”'
* FemaleGaze: Ben spends a lot of the movie sans shirt, and catches some women at his office staring.
* FictionBusinessSavvy: Ben thinks a great new slogan for the diamond industry group is "Go frost yourself."
** Hilariously lampshaded when his boss, agreeing this to be an excellent idea, shouts it out the window, only for someone to shout back "Frost this!"
* FlorenceNightingaleEffect: [[LampshadeHanging Lampshaded in dialogue]].
* FourthDateMarriage: It's not exactly love at first sight.
* ICallHimMisterHappy: Hilariously subverted by having the ''girlfriend'' naming her boyfriend's penis "Princess Sophia". He complains by saying that, if she has to name his parts, it should be a more masculine name, "something like Spike, or Butch, or Krull the Warrior King!"
** [[DeathbringerTheAdorable The last of which is what she names her Chinese crested (which is a small, mostly hairless breed of dog that can conceivably be mistaken for a chihuahua.)]]
* RaceForYourLove: Ben on a motorcycle chasing Andi in a taxi in New York traffic. Guess who wins!
* RageQuit: During a game of buls$%^ at his parent's home on Staten Island, when he discovers his family cheating.
* ShirtlessScene: And in the bathroom, no less. Ben also gets one early in the movie when he changes shirts.
* StrictlyFormula: No surprises in the plot, but still a good romantic comedy.
* UrineTrouble: The movie has Krull the Chinese crested peeing on a pool table.