安迪·安德森 (Andie Anderson) 是一家名为 Composure 的流行女性杂志的作家。 她以撰写有趣轻松的“如何做”文章而闻名，但她渴望解决更严肃的话题。 有一天，她的朋友米歇尔又经历了一次分手，她感到沮丧，认为自己不够有魅力。 安迪不同意并指出米歇尔过于粘人和情绪化的行为才是真正的问题。 受此启发，安迪决定写一篇题为“如何在 10 天内失去男人”的文章来证明她的观点。 她的计划是和一个男人约会，并模仿米歇尔的行为，以便在 10 天内赶走他。

与此同时，广告主管本杰明·巴里 (Benjamin Barry) 想要摆脱他在啤酒和体育宣传方面的日常工作。 他渴望为一家钻石公司领导一场享有盛誉的广告活动。 然而，他的老板菲利普质疑本是否真正理解与钻石相关的浪漫。 作为回应，本打赌，声称他可以让任何女人爱上他。 Phillip 向他提出挑战，要求他在距公司舞会仅 10 天之前实现这一目标。 如果本成功了，他将有机会领导钻石战役。 Ben 的竞争对手 Judy Spears 和 Judy Green 在访问 Composure 杂志办公室时无意中听到了 Andie 的文章。 当他们在酒吧里看到安迪时，他们选择她作为本必须追求的女人。

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本和安迪相遇并开始了各自的任务，但都隐藏了自己的真实意图。 为了完成她的文章，安迪付出了很多努力让本爱上她，然后与她分手。 然而，本对安迪的兴趣越来越大，希望能让她真正爱上自己。 安迪耍花招，比如让本错过尼克斯队比赛的最后一击，让他给她买苏打水，在电影中大声评论，在电影院引起轰动，把她的东西搬进他的公寓，送给他一株蕨类植物 作为他们关系的象征，让他惊讶的是席琳迪翁演唱会的门票而不是尼克斯队的比赛。 尽管如此，安迪偶尔会露出真实的自己，本开始对她产生真挚的感情。

安迪对这个项目感到沮丧，决定扰乱本的男孩扑克之夜，以迫使他与她分手。 然而，Ben 的朋友 Tony 和 Thayer 鼓励他转而向 Andie 寻求夫妻咨询。 安迪邀请米歇尔假扮成夫妻治疗师，在他们的治疗过程中，米歇尔暗示本以安迪为耻。 本反击，邀请安迪周末到史泰登岛与家人见面。 在拜访期间，本和安迪建立了真正的联系和纽带。

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