Bart Got A Room (2009)

Director: Brian Hecker
Genres: Comedy and Teen
Running Time: 1 hr. 20 min.
Starring: Steven J. Kaplan, Alia Shawkat, Jon Polito, Jennifer Tilly, William H. Macy, Cheryl Hines

Plot: While Danny's father and mother independently search for love, Danny is on his own desperate quest to find a prom date. Danny's search becomes progressively more pathetic once he and his family learn that Bart, the school's biggest dweeb, not only secured a date for the prom, but got a hotel room as well.

http://www.imdb.com/title/tt0472050/

Synopsis:
Nerdy high school senior Danny has spent six hundred bucks on the hotel room, the limo and the tux for his prom. He's only missing one thing--the girl. Hampered by well-intentioned but clueless advice from his newly-divorced parents and unsympathetic mocking from his best friends, Danny battles peer pressure, teen angst and his own raging hormones as he desperately searches for a prom date.