The Trouble with Bliss (2011)

Overview
35-year-old Morris Bliss (Michael C. Hall) is clamped in the jaws of New York City inertia: he wants to travel but has no money; he needs a job but has no prospects; he still shares an apartment with his widowed father; and the premature death of his mother has left him emotionally walled up. When he finds himself wrapped up in an awkward relationship with Stephanie (Brie Larson), the 18-year-old daughter of a former classmate, Morris quickly discovers his static life unraveling and opening up in ways that are long overdue.