Some things that happen to us as we are in high school stir us in very different direction and we become persons we never thought we could be. The same thing happened here. After he was rejected by his love and best friend Jamie Palamino (Amy Smart), Chris Brander (Ryan Reynolds), the chubby kid in school, decided to change his life. He moved to Los Angeles and made a successful career as a music manager. He also became one hell of a womaniser, sleeping with another girl every day. One day, as he was stuck with one of the famous music divas, Samantha James (Anna Faris) on the plane that was taking them to Paris but had a malfunction and had to land somewhere, he only had a flight that goes straight to his home town. Of course, he takes this blonde music diva to his home, meeting her with his parents and hoping that no one would see him. In a bar near by, where he comes for a drink, he encounters his old love again- Jamie. This time, he decides that he isn't going to be satisfied with "I love you like a brother" and "Just friends, right?". He is determined to win her over when another player comes into the game- Dusty Dinkleman (Chris Klein). With the rival right there in front of his eyes, Chris decides to make the best out of himself and get the girl.
Jennifer Lawrence might join Chris Martin on tour
