When Doug married Hailey - beautiful, smart and ten years older - he left his carefree Manhattan life to live in the suburbs with Hailey and her teenage son, Russ. Three years later, at 29, Doug has been a widower for twelve months and just wants to drown himself in self-pity and Jack Daniels. But his family has other ideas... Russ is furious with Doug for not adopting him, and has fallen in with a bad crowd. Claire, Doug's irrepressible, pregnant twin sister, has left her husband and, uninvited, moved in with Doug. And their sister Debbie is determined to have the perfect wedding, at any cost. Soon, Doug finds himself trying to forge a relationship with Russ, reconnect with his own eccentric family, and reluctantly edges back into the complicated world of dating...