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Chris (Reynolds), an obese but good hearted teenager is humiliated when his unrequited love for his best friend, the beautiful cheerleader Jamie (Smart) is publicly exposed. A decade later the now adult Chris is a thin, handsome and slick ladykiller and successful record producer in Los Angeles who forced by his boss to escort lunatic pop diva Samantha James (Faris) to Paris. When Samantha accidentally causes the plane to catch fire, they are forced to land in Chris's hometown where he soon re-encounters Jamie...
This movie contains examples of:
- Amusing Injuries
- Annoying Younger Sibling: Chris's teenage brother Mike.
- Bitch in Sheep's Clothing: Dusty Dinkleman.
- Brick Joke: "Hello, Joyce?"
- Cloudcuckoolander: Samantha and Chris's mother. The latter is merely a bit spacey while the former is near psychotic.
- Covers Always Lie: While the main plot does feature a Love Triangle, Anna Faris's character is not part of it - she has a thing for Chris but he is never even slightly attracted to her.
- A Date with Rosie Palms: Mike.
Chris: You have her poster on your wall?
Mike: Yeah. I slapped the ham to it, like, an hour ago.
Mom: Mike? What ham did you slap? Not the ham I just bought?
- Deadpan Snarker: Chris. Well he is being played by Ryan Reynolds.
- Dumb Blonde: Samantha in contrast to the intelligent, grounded Jamie.
- Groin Attack: Repeatedly - Chris by an oxygen tank in the ambulance; Mr. Palomino (Jamie's dad) by a falling reindeer from his Christmas display; Chris by Samantha and her tazer gun.
- Hey, It's That Guy!: Chris works for Bill Dauterive and is the son of Elaine.
- Hopeless Suitor: Chris was this Jamie in high school.
- Jerk Jock: Tim. Ten years after high school, he's seen hanging around the bar, balding and still wearing his letter jacket.
- Jerk with a Heart of Gold: Chris. Though the 'Heart of Gold' part might not be so obvious at first.
- Just Friends: The Movie.
- Les Yay: Samantha kissing Darla and saying that she "likes girls".
- Not Good with Rejection: Samantha towards Chris. She tazers him in the groin when he tries to reject her.
- The Prima Donna: Samantha.
- Rich Suitor, Poor Suitor: A rare case where the good(ish) guy is the rich suitor.
- Shout-Out: "I'm Samantha James, bitch!"
- Small Name, Big Ego
- Unlucky Childhood Friend: Chris to Jamie.
- Yandere: Samantha.