Nick and Norah's Infinite Playlist is just about as quirky indie as you can get. It stars Michael Cera as awkward Nick, the only straight guy in the gay punk band The Jerkoffs, and Kat Dennings as rich girl Norah, the daughter of famed music producer Ira Silverberg. Nick recently broke up with his girlfriend of 6 months Tris (who has also been cheating on him for 6 months) and is taking it pretty hard. He makes her mix tapes, which she just throws away, only to be picked up and adored by Norah. They meet at one of his band's concerts and Norah asks him to pretend to be her boyfriend for five minutes. And so begins the night. And just like every teen romantic comedy, they fall in love, fall out of love, and both eventually redeem themselves and partner up again.

IMDb link: http://www.imdb.com/title/tt0981227/