Drive Me Crazy (1999)

Nicole Maris is a popular high school preppy senior in Utah who gets her life turned upside down when her perfect date, Brad, falls for a cute cheerleader from another school a month before the school's centennial senior prom. After recovering from the shock, Nicole comes up with a solution to save her reputation: find a guy to appear like they're going steady and to take her to the dance hoping to make Brad jealous. Nicole then hooks up with her next door neighbor, prankster and trouble maker Chase Hammond, and tries to model him in her own image while he's looking to make his long-term girlfriend Dulcie jealous too. However, both Nicole and Chase don't expect their charade to lead it where they never expected it to.