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Based on a short cartoon book of the same name by Michele Alexander and Jeannie Long, this light Romantic Comedy film was directed by Donald Petrie (of other Chick Flick's such as Miss Congeniality, and Mystic Pizza), 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 Hilarity Ensues.
The film contains examples of:
- Alliterative Name: Andie Anderson.
- Benjamin Barry too.
- Baby Talk: Andie uses this as one of the methods to make men run away fast.
- Based on an Advice Book: Well, actually a woman's magazine in this case.
- Best Friend Manual: 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.
- The Bet: Andie makes one with her boss. Ben makes one with his boss. 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.
- Chick Flick: Oh, Matthew, take that shirt off!
- Deathbringer the Adorable: Krull, looking natty in his Burberry sweater!
- Defcon Five: "I have to crack this guy. I mean, this is Defcon Five, and I have to do something truly appalling. It's not funny."
- Everyone Loves Blondes: Andie Anderson is so gorgeous she 'could throw up on a guy and he'd say, “Do it again.”'
- Fiction Business Savvy: Ben thinks a great new slogan for the diamond industry group is "Go frost yourself."
- Female Gaze: Ben spends a lot of the movie sans shirt, and catches some women at his office staring.
- Florence Nightingale Effect: Lampshaded in dialogue.
- Fourth Date Marriage: It's not exactly love at first sight.
- I Call Him "Mister Happy": 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!"
- Please Dump Me
- Race For Your Love: Ben on a motorcycle chasing Andi in a taxi in New York traffic. Guess who wins!
- Rage Quit: During a game of buls$%^ at his parent's home on Staten Island, when he discovers his family cheating.
- Shirtless Scene: And in the bathroom, no less.
- Strictly Formula: No surprises in the plot, but still a good romantic comedy.
- Urine Trouble: The movie has Krull the Chinese crested peeing on a pool table.