Tae-Il (Hwang Jung-Min) lives a fast life as low level thug. He then learns that he has a terminal illness and not much time left to live. For the first time in his life falls in love. The woman's name is Ho-Jung (Han Hye-Jin).当男人恋爱时》讲述的是三流小混混泰日（黄政民 饰）一直以来过着帮高利贷讨债的不务正业的生活，直到遇见了好静（韩惠珍 饰），才第一次感受到什么是爱情。而好静也被泰日的纯情所打动，慢慢打开心房，和泰日展开一场浪漫爱
