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 a popular socialite up on the latest fashions; Chase is an unpopular activist and trouble-maker on the latest protest. Nicole wouldn't miss a pep rally or basketball game with her scheming socialite friends. Chase can usually be found in a dark coffee room with his friends.Nicole wants a dream date with the star basketball player for their school's senior prom, 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 not joining her in animal rights activism. Now that they have something in common, Nicole and Chase reluctantly join forces to navigate the land mines of high school love.
Nicole and Chase's scheme is to publicly date each other to attract the interest and jealousy of their respective romantic prey. Chase allows Nicole to do a makeover of himself to make himself more handsome and presentable to the other social circles at the school. At first, their scheme works: they both get the person they wanted. But in the midst of planning a gala centennial celebration for prom, Nicole and Chase find that the one they always wanted is closer than they ever realized. Finally, they dump their original dates and fall in love with each other.
There is still one big twist that could ruin their relationship forever in the end. After the celebration ends, they go back home only to find out that their parents have fallen in love and will move in together, which would make them step-siblings. However, the movie ends with the feeling that they aren't going to let that fact stop their relationship.
- Melissa Joan Hart as Nicole Maris
- Adrian Grenier as Chase Hammond
- Stephen Collins as Mr. Maris
- Susan May Pratt as Alicia DeGressario
- Mark Webber as Dave Ignazzi
- Kris Park as Ray Neeley
- Gabriel Carpenter as Brad Seldon
- Ali Larter as Dulcie
- Lourdes Benedicto as Chloe Frost
- Keri Lynn Pratt as Dee Vine
- Natasha Pearce as Sue Ryan
- Jordan Bridges as Eddie Lampell
- Keram Malicki-Sánchez as Rupert
- Mark Metcalf as Mr. Rope
- William Converse-Roberts as Mr. Hammond
- Faye Grant as Mrs. Maris
- James Van Der Beek as Basketball Player (uncredited)
- Elizabeth Hart as Vixen #2