安迪·安德森是一位才华横溢的作家,为一本名为《Composure》的流行女性杂志撰稿。 她以撰写“如何做”文章的专业知识而闻名。 但内心深处,她感到没有成就感,渴望解决更有意义的课题。 有一天,她的朋友米歇尔再次经历了心碎,她认为这是因为她不够有吸引力。 安迪不同意,并认为米歇尔过于情绪化和粘人的行为正在赶走男人。 受此启发,安迪想出了一个大胆的计划来证明自己的观点。
与此同时,广告主管本杰明·巴里 (Benjamin Barry) 希望摆脱平时的啤酒和体育活动,与一家钻石公司达成一项享有盛誉的广告协议。 他的老板菲利普质疑本是否真正了解与钻石相关的浪漫。 对此,本自信地宣称他可以让任何女人爱上他。 菲利普要求他在 10 天后即将举行的公司舞会上这样做。 如果本成功,他将有机会领导钻石运动。 他们几乎不知道,本的两个竞争对手朱迪·斯皮尔斯和朱迪·格林无意中听到了安迪在《冷静》杂志上的任务,并看到了在他们的计划中利用她的机会。
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本和安迪相遇并开始各自的任务,但没有透露他们的真实意图。 安迪开始努力让本为她神魂颠倒,然后在十天内与她分手以完成她的文章。 另一方面,本留下来,希望让安迪真正爱上他。 安迪使出了各种各样的伎俩,比如让本错过重要时刻,让他尴尬,甚至在他们的关系中引入随机元素,比如蕨类植物和狗。 然而,在她的游戏中,安迪的真实个性闪耀出来,本开始对她产生真正的感情。
安迪对整个项目感到沮丧,在本和朋友们的扑克之夜期间,安迪达到了崩溃的边缘。 她发脾气,希望这能促使他结束事情。 但本的朋友托尼和塞耶敦促他为他们的关系而奋斗,并建议夫妻向安迪进行咨询。 安迪不顾一切地想要维持这个谜题,于是邀请米歇尔假扮他们的治疗师。 在会议期间,米歇尔无意中让安迪知道了这个赌注。 安迪决心揭露本的真实意图,他同意去斯塔滕岛与他的家人见面。 当安迪和本在一起度过一段时光时,他们开始建立真正的联系。
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