在这部自由之丘剧情片中,待业青年栗原八相信人生万般皆由命运，并亲自证实自己的理论，在东京一隅的自由之丘，八再次遇见了前日演唱过一首名叫《自由之丘》歌曲的小酒吧歌手里奈，上回他曾试图搭讪而未果，这次却奇迹般地和她发生了一夜情，这何尝不是命运使然？ 里奈问八平常做什么，八说，自由的人。
俊曾经梦想成为一个自由的人。他为寻找新的生活来携新婚妻子和女儿来到这座城市，几年后却发现被他曾向往的成功生活所束缚。俊在里奈身上，看见了一种自由的可能性，即不离不弃地遵循着自己的梦想，虽然它并不似能为自己带来什么。
里奈默默无名地在小酒吧演唱。似在追逐自己梦想，却又看不到未来。孤独的她与各种男人交往，在八身上看见无所事事的随意，又从俊窥见按部就班的规划。三人从彼此身上看见一种慰藉。是随波逐流，还是向曾有过的梦想迈出一步，去追寻一种自由？
Looking forward to a new kind of life, Jun took his young family to Tokyo. Five years later he finds himself trapped by his repetitive routines, developing a discrete affair with a small bar singer, Rene, from whom Jun sees a light of freedom and the possibility of living one's passion. Hachi the 'wanna-be' singer happens to come across Rene singing on stage, and coincidentally sees her again at a place called Freedom Hills. Both men set out to make a difference to their lives, in pursuit of that freedom, but will anything change? A story about pursuance of self and the things we could do in life, dissected from moments of intersection between three people under the city lights of Tokyo.
