Ghost World (2001)

With only the plan of moving in together after high school, two unusually devious friends seek direction in life. As a mere gag, they respond to a man’s newspaper ad for a date, only to find it will greatly complicate their lives.

Tags: Bob Balaban, Brad Renfro, Comedy, Drama, Illeana Douglas, Scarlett Johansson, Steve Buscemi, Thora Birch