The Inevitable Death of Gus Banister (2009)

Gus Banister, a depressed 23 year old has no job, he's haunted by the memory of the girl who got away, and he's drinking all of his problems away. He just bombed his big pitch meeting to produce his script, when his friend as a serious joke signs him up to the be a mentor to an orphan. After a few meetings with the orphan, Gus finds out, he may be the father of the child.