富家子张泰林（张智霖 饰）在偶然之下结识了俏护士邝美宝（刘心悠 饰），两人堕入爱河，但其后泰林却逐渐发现美宝的另一面：多疑、善妒、控制欲强兼有轻微的暴力倾向。泰林难以忍受提出分手，但依然受到美宝的跟踪。美宝在医院偶遇泰林前女友慧欣（苟芸慧 饰），得知泰林不为人知的秘密，而此时泰林与母亲介绍相亲的女孩晴晴（叶熙祺 饰）的关系越加亲密。一次巧遇，美宝与泰林公开对质他的秘密，原来这场疯狂爱情才刚刚开始……

Tom, greeting-card writer and hopeless romantic, is caught completely off-guard when his girlfriend, Summer, suddenly dumps him. He reflects on their 500 days together to try to figure out where their love affair went sour, and in doing so, Tom rediscovers his true passions in life.