In a city that never sleeps, Marty (Ron Livingston) is getting too much sleep and not enough action. No work, no money, no women... no life! Despite his best friend Dave's (Bray Poor) efforts to cheer him up, Marty is ready to pack up and leave Manhattan for a safe but unfulfilling life in his hometown of Maine. Just as he's lost all hope, Marty meets Nina Cohen (Cara Buono) and then Nina Harris (Amanda Peet); two dynamite but very different girls who fall head over heels for him. Dave, a smooth talking playboy, is incredibly impressed. Marty's live seems to be taking on the most delicious complications, until he realises that he's falling for both women and suddenly love creates more problems than one man can handle.