History YMMV / HowToLoseAGuyIn10Days

* MemeticMutation: In the Latin American countries it's popular the line "Bullshit[[note]]Translated as ''Patrañas'' in the Mexican dub[[/note]]." from the card scene.

* SugarWiki/FunnyMoments: After their first date, Andie and Ben respectively [[TemptingFate tempt fate]].
--> '''Ben:''' (To himself, whilst waving to her) Ooh, you are falling in love with me already.\\
'''Andie:''' (To herself, whilst waving back) I'm gonna make you wish you were dead.
** King Krull, the Chinese-crested.
** Andie and her co-workers making fun of how their boss has a bad habit of popping in on them during lunch.
** When Andie claims [[BlatantLies she's vegetarian]] ''just as Ben presents her with a lamb roast he cooked himself''. She even starts woefully singing "Mary had a Little Lamb" and gagging.
** Later, at a strictly vegan restaurant, while Andie is away, Ben gargles water to get rid of the bland taste, whilst he covers his meal in salt for flavor.
** Andie's album of hers and Ben's photo-shopped "memories". One of the photo-shopped faces is a little boy grinning his gap-toothed smile as wide as he can.
---> '''Ben:''' Our kids are really... attractive.
** According to his mother, Ben wore diapers until he was five years old. He nearly chokes on his drink when Andie brings this up.
** Ben discovering that Andie has filled his bathroom cabinet with ''her stuff''. Naturally, he doesn't take it well.
---> '''Ben:''' (disgusted) Aw, no, no, nooo!
** Andie disrupting Ben's Poker game with his friends.
*** The "[[MakesSenseInContext Love Fern]]".
----> '''Andie:''' Oh no. Our Love Fern! It's ''dead''...\\
'''Ben:''' ({{Beat}}) No, honey, it's just [[BlatantLies sleeping]].
** The part where Michelle must pretend to be a couple's counselor. What makes this comical is that the roles are switched: Andie has to play the overemotional girl while her friend plays the sane one. It's In-Universe PlayingAgainstType.
** After learning the truth, Ben and Andie have an argument in the form of a duet singing "You're So Vain". Rather badly.
** Andie storms out of the party still wearing the priceless necklace she was loaned for the evening. As she and Ben are yelling at each other a security guard runs up to them and forces himself to interrupt.
--->'''Security Guard:''' Please, just give me the necklace. Then you can go on a kill each other.
* SugarWiki/HeartwarmingMoments:
** In the beginning, one of Andie's more serious writings are about ways a warring country could make peace.
** During their visit to his family in Staten Island, Ben's mother reveals that Andie is the first girl he's ever brought home to his family.
** Even before that, Andie and Ben bonding over his family's favorite card game. It's the first time Andie drops her façade as a clingy, sensitive cringe-worthy girlfriend.
** Ben's quiet delight at learning second-hand that Andie loves him. Not because he's won a bet, but because he loves her back.
--->'''Ben:''' She loves me?
** [[spoiler: When Michelle's boyfriend comes back to her, especially because, despite her clingy nature, he missed her during their breakup.]]

* TearJerker:
** It's rather painful to watch as Andie and Ben simultaneously learn about the bet and the magazine article (respectively). They both [[BecomingTheMask fell in love with each other]], and it hurts that just as they learned the other genuinely loved them, it's undone by the bitter truth.
** Before this, Andie has a change of heart when she realizes she's fallen for Ben. He's unaware that he is part of her project to 'lost a guy in 10 days', and she's feeling awfully guilty about manipulating the one guy she's fallen for.
** "Because [[ArmorPiercingResponse you can't lose something you never had]]." What makes it even sadder is that she's lying to herself. She ''did'' have him, because he fell in love with her and she him. As she walks away, you can see her covering her face with her purse probably so Ben won't see her crying.

* WhyWouldAnyoneTakeHimBack: A ''double'' example in which ''both'' partners start the relationship under false pretenses. Both halves of the deception are revealed; both parties are hypocritically furious and dump each other, then decide in the end that they're meant to be together after all. Though it could be argued that in that case, they ''deserve'' each other.

*** Later, at a strictly vegan restaurant, while Andie is away, Ben gargles water to get rid of the bland taste, whilst he covers his meal in salt for flavor.

* SugarWiki/HeartwarmingMoments: In the beginning, one of Andie's more serious writings are about ways a warring country could make peace.

* TearJerker: It's rather painful to watch as Andie and Ben simultaneously learn about the bet and the magazine article (respectively). They both [[BecomingTheMask fell in love with each other]], and it hurts that just as they learned the other genuinely loved them, it's undone by the bitter truth.

** "Because [[ArmorPiercingResponse you can't lose something you never had]]."

** According to his mother, Ben wore diapers until he was 4 years old. He nearly chokes on his drink when Andie brings this up.

--> '''Ben:''' Our kids are really... attractive.

--> '''Ben:''' (disgusted) Aw, no, no, nooo!

--> '''Andie:''' Oh no. Our Love Fern! It's ''dead''...
--> '''Ben:''' ({{Beat}}) No, honey, it's just [[BlatantLies sleeping]].

--> '''Ben:''' She loves me?

* JerkassHasAPoint : Andie's boss at the magazine. It's a magazine devoted to fashion, makeup, and how-to articles. Why would Andie think "serious journalism" has a place there? Didn't she read the magazine before she took the job? The movie inadvertently implies she's either an entitled idiot who felt she could write whatever she want despite her workplace's needs, or was not a good enough writer to land a job at the sort of "serious" publication she obviously wanted but still entitled enough to think the "trivial" magazine should let her do as she pleased.

* WhyWouldAnyoneTakeHimBack: A ''double'' example in which ''both'' partners start the relationship under false pretenses. Both halves of the deception are revealed; both parties are hypocritically furious and dump each other, then decide in the end that they're meant to be together after all. Though it could be argued that in that case, they ''deserve'' each other.
* WordOfGod / WordOfSaintPaul: According to actress Kate Hudson, about the fate of characters Andie and Ben, they would have gotten married with kids. They'd probably be miserable right now too.

* WhyWouldAnyoneTakeHimBack: A ''double'' example in which ''both'' partners start the relationship under false pretenses. Both halves of the deception are revealed; both parties are hypocritically furious and dump each other, then decide in the end that they're meant to be together after all. Though it could be argued that in that case, they ''deserve'' each other.

* JerkassHasAPoint : Andie's boss at the magazine. It's a magazine devoted to fashion, makeup, and how-to articles. Why would Andie think "serious journalism" has a place there? Didn't she read the magazine before she took the job?

* MemeticMutation: In the Latin American countries it's popular the line "Bullshit[[note]]Translated as ''Patrañas'' in the Mexican dub[[/note]]."

--> '''Ben:''' (disgusted) Aw no! Nooo!

** The part where Michelle must pretend to be a couple's counsilor. What makes this comical is that the roles are switched: Andie has to play the overemotional girl while her friend plays the sane one. It's In-Universe PlayingAgainstType.
** After learning the truth, Ben and Andie have an argument in the form of a duet singing "You're so vain". Rather badly.

** During their visit to his family in Staton Island, Ben's mother reveals that Andie is the first girl he's ever brought home to his family.

* CrowningMomentOfFunny: After their first date, Andie and Ben respectively [[TemptingFate tempt fate]].
--> '''Ben:''' (To himself, whilst waving to her) Ooh, you are falling in love with me already.
--> '''Andie:''' (To herself, whilst waving back) I'm gonna make you wish you were dead.

* CrowningMomentOfHeartwarming: In the beginning, one of Andie's more serious writings are about ways a warring country could make peace.

* DesignatedHero: We're supposed to root for both the leads even though they have no problem doing something so nasty to another person that could damage their self-esteem and ability to trust.

* "Because [[ArmorPiercingResponse you can't lose something you never had]]."

* "Because you can't lose something [[ArmorPiercingStatement you never had]]."