Clueless(1995)

If anyone in Beverly Hills is clued in, it's Cher. She's almost 16, she's rich, she's way popular, and she loves letting the world benefit by her expertise in all of life's important issues--like dating, fashions and looking good. During this school year, however, Cher is going to feel her sense of control slipping as she discovers that the world is too chaotic to be manipulated by even someone as supremely clued in as she is. She's going to discover that, when it comes to matters of the heart, she's... clueless.