托尼展示了本·安迪 (Ben Andie) 发表的文章，她在文中承认失去了她唯一爱上的男人。 本深受感动，意识到自己的错误以及他对安迪的感情之深。 他决心不让她溜走，追上她的出租车并与她对峙，指责她逃跑。 在那个由衷的时刻，他们都坦白了彼此的真实情感。 本指示出租车司机归还安迪的物品，并宣布他将陪同她。 他们分享了一个热情的吻，结束了他们的重新联系，并承诺重新开始。

安迪·安德森 (Andie Anderson) 是一家名为 Composure 的流行女性杂志的作家。 她以撰写“How to”文章的专业知识而闻名，但她对同样的老话题感到厌倦。 有一天，她的朋友米歇尔经历了另一次分手，她对自己感到沮丧，认为自己不够有吸引力。 安迪不同意并认为米歇尔对男人的粘人和过度情绪化的行为才是真正的问题。 受此启发，安迪想出了一个计划，写一篇名为“如何在 10 天内失去一个男人”的文章来证明她的观点。 她决定和一个男人约会，并故意在 10 天内像米歇尔一样把他推开。
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与此同时，广告主管本杰明·巴里 (Benjamin Barry) 想摆脱他的日常项目，为一家钻石公司领导一项享有盛誉的广告活动。 然而，他的老板菲利普怀疑本对浪漫的理解，并挑战他让任何女人爱上他。 如果本能在 10 天后的公司舞会前做到这一点，他将有机会领导钻石活动。 本的同事和竞争对手朱迪·斯皮尔斯和朱迪·格林在访问《镇静》杂志办公室时了解到安迪的计划。 在酒吧里看到安迪，他们选择她作为本必须追求的女人。

本和安迪在没有透露他们隐藏动机的情况下相遇。 安迪付出了很多努力让本爱上她，然后为了她的文章与她分手，而本则试图让她真正爱上他。 安迪使用了各种策略，比如让本错过一场重要的篮球比赛，在电影院引起一场戏，把她的东西搬进他的公寓，甚至带他去看席琳迪翁的音乐会而不是尼克斯队的比赛。 尽管她很努力，但安迪的真实个性有时会闪耀出来，本开始对她产生真实的感情。
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