Bart Got A Room (2008)

The plot is centered on the hopelessly dateless Danny (Steven Kaplan), a gawky band nerd who must decide between taking his best friend, Camille (Alia Shawkat), to the prom, and attempting to woo the date of his dreams, a pretty blonde cheerleader. Along the way he endures derision and peer pressure from friends, as well as uncomfortably frank advice from his divorced parents, played by Cheryl Hines and William H. Macy.