然后我们有本杰明·巴里（Benjamin Barry），这位广告人想要证明他不仅仅可以处理啤酒和体育广告。 他想领导这场大型钻石运动，但他的老板怀疑他对浪漫的了解。 于是，本和他的老板打赌，他可以在十天内让任何女人爱上他。 如果他成功了，他就能领导钻石运动。 现在，事情变得有趣了：本的竞争对手朱迪·斯皮尔斯和朱迪·格林知道安迪的计划，他们选择她作为本必须浪漫的女人。

于是，本和安迪相遇了，但他们都不知道对方的真实意图。 安迪竭尽全力让本爱上她，然后与她分手，这样她就可以写她的文章了。 但本很喜欢她，并希望她爱上他。 安迪做出了各种疯狂的特技，比如让本错过尼克斯队的比赛，让他在电影院被击倒，甚至把她的东西搬进他的公寓。 她带他去参加席琳·迪翁音乐会而不是篮球比赛，但有时她的真实个性会闪耀出来，那就是本开始爱上她的时候。
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最终，安迪厌倦了整件事，并试图在本的扑克之夜大吵大闹，试图让本和她分手。 但本的朋友建议进行夫妻咨询，安迪的朋友米歇尔假装是治疗师并引发了一些戏剧性事件。 本提议将安迪介绍给他的家人，在拜访期间，他们实际上开始真正建立联系。

他们一起去参加这个精美的公司舞会，安迪与本的老板交谈，老板告诉他安迪爱他，他赢了。 但这就是事情变得混乱的地方：朱迪和朱迪泄露了安迪知道这个赌注并且正在配合的秘密。 安迪发现后，在聚会上，她试图在所有人面前羞辱本。 他们最终在舞台上争吵并分手。
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