Synopsis/Details
MAX (14), socially awkward, is pawned off to his wacky neighbors (The Leons) for the summer by his vacationing parents. With a serious crush on CASSIDY LEON (14), extremely quiet, who lives there, Max finds this an excellent opportunity to try and make her his girlfriend. But his fear of talking to girls makes what seems easy, impossible. Determined to make her his girlfriend, he seeks his co-worker BRANDON (17), cool, to teach him how to talk to girls. In return, Max agrees to be Brandon's inside man with Cassidy's older sister LEANNE LEON (17), promiscuous, who Brandon has the hots for. Max also makes another deal with Leanne's friend MARIE (17), too much make-up, talks a lot, to help her get Brandon who she likes, in return for her teaching him to kiss.
Brandon pushes Max to try to pick up a married woman and a nun to train him to conquer his fear, which helps him a little. Max sets up a double date with Cassidy, Marie, and Brandon, which goes terrible, and after it's done Marie ferociously makes out with Max turned on from interacting with Brandon earlier, giving Max his first experience with a woman. Having made little progress with Cassidy and summer drawing to a close, things go further downhill for Max when he's exposed for playing Brandon and Marie, knowing both of them couldn't get what they want.
With everyone mad at him, Max goes for a walk and is kidnapped by Leanne's boyfriend who thinks Max hooked up with Leanne. Leanne's boyfriend ties Max to the top of the town gorge as a ransom for Leanne to go on tour with his band. Flocks of people crowd to the bottom of the gorge and spectate. Brandon and Marie forgive Max from the crowd, and Cassidy speaks to him for the first time. Cops try to rescue Max but don't succeed because he falls from the top of the gorge and breaks his leg. After recovering, Max reminisces about a great summer. No longer afraid of girls and now friends with Cassidy, he says he's okay with not having a girlfriend for the time being.
