The battle for the Five Points nears when Bill Cutting decides to reconcile with his estranged wife and son. Trying to put the past behind them and wishing to go on with life together all while ruling the Five Points can be a challenge. Things are then made harder when a bit from Bills past comes to haunt him.

Lip Gallagher is back home after being kicked out of college. He is buying cigarettes from a bodega when he sees the woman he knew he could spend the rest of his life with. At first he only wanted to sleep with her but with his drinking problems and her troubled past come back to haunt her will they get through the obstacles that get in the way of their true feelings?