Nicole Maris (Melissa Joan Hart) and Chase Hammond (Adrian Grenier) live next door to each other. Nicole lives with her divorced mother and Chase’s mother died of cancer, making them two teens living with their single parents. However, they are worlds apart. Nicole is up on the latest fashions; Chase, on the latest protest. She wouldn’t miss a pep rally or basketball game with her scheming socialite friends; he can usually be found in a dark coffee room with his friends who don’t care what they wear.
Nicole wants a dream date with the star basketball player, but right before it was certain they were going together, he falls in love with a cheerleader. Meanwhile, Chase’s “non-conformist” girlfriend, Dulcie (Ali Larter) dumps him for another man. Now that they have something in common, Nicole and Chase reluctantly join forces to navigate the land mines of high school love….