Plot Points
Iconic Scenes and Quotes
Characters' Twists
100

Andie starts dating Ben for this reason

for her article on how to lose a guy in 10 days

100

Andie gives Ben a nickname that he hates throughout the movie.

Benny-Boo-Boo

100

Describe Andie Anderson’s job and what motivates her to start dating Ben Barry.

Andie Anderson is a "How-To" columnist for Composure magazine. She starts dating Ben to write an article called "How to Lose a Guy in 10 Days."

200

Ben begins dating Andie to win this.

a bet to win the diamond campaign

200

In an attempt to drive Ben away, Andie brings him to this public event.

a couples therapy session

200

What is Ben Barry’s career goal at his advertising agency, and how does it lead him to Andie?

Ben Barry is an advertising executive aiming to land a big diamond campaign. He bets his bosses that he can make any woman fall in love with him in ten days, which leads him to date Andie.

300

The climax of the movie takes place during this special company event.

diamond company’s gala

300

Andie shows up with a dog she names after this condiment.

Krull the Warrior King

300

How does Andie’s relationship with her friend Michelle play into her article?

Andie is inspired by Michelle’s recent breakup to write her article about how to purposefully ruin a relationship in ten days.

400

In order to annoy Ben, Andie does this while they’re watching a basketball game.

yell and cheer for the wrong team

400

Andie delivers this memorable line when Ben brings her to his family home.

"You can't lose something you never had"

400

Describe the type of chemistry between Andie and Ben at the beginning of their relationship. How does it evolve as they get to know each other?

Initially, Andie and Ben’s relationship is filled with playful yet strategic tension, as each tries to manipulate the other. Over time, their connection becomes genuine as they inadvertently fall for each other.

500

Ben realizes the truth behind Andie’s article when he sees this item at the gala.

the How to Lose a Guy in 10 Days' magazine cover

500

Andie embarrasses Ben by doing it.

singing "You're So Vain" in public.

500

Explain how the careers of Andie and Ben play a role in the challenges they face in their relationship.

Andie’s career as a columnist drives her to create unrealistic scenarios to drive Ben away, while Ben’s career as an advertiser makes him equally focused on "winning" Andie for a work-related bet. These professional motivations create misunderstandings and tension that they must overcome.

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