A man in his early forties is unable to sleep as he contemplates the decision of running for mayor of his small town. While considering his options, his thoughts drift to his wife and their devoted relationship. As he reflects on his good fortune, one fact becomes apparent-his relationship with his wife originated even before it began. In 1992, life is anything but predictable for fifteen-year-old Scott Furman as he comes of age in his Midwestern small lower-class town of South Hillside. An incident that happened when he was born haunts his parents, making his mother's emotional turmoil a mystery. While dealing delicately with his mother, Scott's sensation of being an incomplete person also mystifies him. On the first day of summer vacation, Scott meets a girl named Briana from the adjacent wealthy town of North Hillside. Intelligent hardworking Scott and shy reserved Briana quickly realize their true love is authentic. When they learn of their family and friends' stereotypical feelings of the other one's town, Scott and Briana wisely keep their relationship a secret. However, when Scott's best friend, Derek, learns about Briana, the boys' friendship becomes a battle of wits. Self-centered and competitive, Derek takes pleasure in charming the girls of Scott's interest. One girl unmoved by Derek's charm is Scott's sister-like friend, Felicia. Growing up together, Scott and Felicia have a special bond, but Scott's overprotectiveness of Felicia causes additional complications, especially when Felicia realizes she has always loved Scott. With the love of two girls, Scott's life is full of twists and surprises.