Brooklyn, 1985. With the mob world as a backdrop, three life-long friends struggle with questions of love, loss and loyalty.

A young pickpocket in the New York subways, living a fast, free, lifestyle is confronted by a woman whom he had a one night affair with, she informs him that she is now pregnant with his child, he must now choose between continuing the lifestyle he lead or take responsibility for his actions.

In this coming-of-age comedy, Tim Dunphy is leading a go-nowhere existence, spending his days smoking pot and hanging out with his best friend, Drugs Delaney. But Tim’s lazy days of getting high are jettisoned after a brush with the law convinces his blue-collar dad to send him to a Connecticut prep school. The one saving grace of the new school is Jane, a fellow student Tim falls for immediately.