Jenny Taylor (played by Amanda Bynes) has found her ideal man who she just knows would sweep her off her feet. The only problem? He's Jason Masters (Chris Carmack), the world's biggest rock star. Hoping for a chance to get close to her idol, Jenny takes a job in her favorite Caribbean resort in St. Luchas with Ryan (Jonathan Bennett) her best friend. When Jason is washed overboard in a storm, Jenny jumps in to save him and the pair find themselves stranded on a seemingly-deserted tropical island. Jenny discovers that they have landed mere miles away from the resort, but instead of telling Jason the truth she lets him believe they are stranded so she can make him fall in love with her. After she discovers her plan, her arch-rival Alexis (Jamie-Lynn Sigler) pretends to be marooned as well.

As Jenny's plans fall apart, she begins to realize that her perfect love may have been with her all along. While Ryan had been helping her by giving her things to survive on the island (like food and makeup), his friend gives him advice on how to woo Jenny since he is in love with her. He completely transforms himself and when she sees him, all she talks about is Jason. Ryan starts to feel bad and begins to leave, but he stops the car midway, gets off and kisses her. He tells her they are perfect together and confesses his love for her, but Jenny protests that they are friends. Upon hearing this, he feels bad and leaves her standing alone as he gets into the car and tells her that he is going back home. She feels bad and goes and tells Jason everything (on the other side of the island) and he promises to sue her before leaving.

She is still on the other side of the island, when Ryan begins to pack his things and go back home. At that moment, the resort receives news that a storm is going to hit St. Luchas Puerto Plata on the side where Jenny is. Unaware of the news, Jenny sits on a branch when the storm hits. Upon hearing about the storm, Ryan rushes onto the other side to save her. When he reaches there, the storm has already hit, so he takes Jenny into the jungle separating the resort and the beach, and lights a fire to keep her warm. After this moment, Jenny realizes that he is the one that cares for her the most. She comes back to the resort with Ryan after the storm is over and sees that the whole resort is practically destroyed. When Jenny and Ryan reach the lobby, Jason and his manager pull her inside a room, where they tell her that they need her help and that they are holding a press conference to tell everyone about the case. When she is about to answer, Ryan bursts inside the room and tells Jason that whatever he does, he should not lose Jenny and that she will be the best girl Jason will ever meet.

After that he confesses his love for Jenny and then is forced/carried out by Jason's bodyguard Gail (Leonardo Cuesta). During the press conference, when Jenny sees Jason lying about everything that happened on the island, she just wants to get it over with. She tells them all that Alexis is his girlfriend and that they are going to get married, and declares to everyone that her real boyfriend is Ryan and then walks up to him and kisses him after both exchange words. Then we see them walking down the resort and dancing. The movie ends by showing us a concert of Jason's in which he unhappily dedicates a song to his wife Alexis Masters.