人到四十的香港某中学国文教师林耀国（张学友）是业已消失的“好好先生”。念书时是学校里有名才子的他，如今面对飞黄腾达、闲来便会打打高尔夫球的昔日同窗，只收获了一份难言的失落，但在他的“坏学生”胡彩蓝（林嘉欣）眼中，他却是有内涵的成熟魅力男。 胡彩蓝身上有几分林耀国妻子文靖 （梅艳芳）当年的影子，她的大胆示爱令林耀国勾起一段深埋在心底的往事，触动心中伤痛，当年的浪漫诗意梦想渐渐只能压在箱底，而选择承担下的本不属他的责任却一背背了二十年。外加其它突如其来的事，一时令他无所适从，然而他却必须作出选择。
Yiu-Kwok is a high school teacher, having a perfect family. Good times don't last long, when a student, Choy-Nam, falls in love with him. For dealing with a relationship with Mr. Seng, a beloved teacher of the couple, his wife Man-Ching requests a leave for a month. A midlife crisis mixing with pressure sends him into an emotional tailspin. Everything seems to lead him towards Choy-Nam, the forbidden fruit. History seems to repeat itself.
黑白灰——《男人四十》。四十而惑。高中男语文老师是个性感的职业。中年男人的色与戒。究竟有没有人看明白的啊！。男人四十。有一句很不要脸的话不知道当讲不当讲。嘉欣的〈男人四十〉。岁月危机。重阳偶拾。
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