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，然后故意把他赶走。 然而，本仍然决心让安迪爱上他。 安迪耍了各种把戏，比如让本在尼克斯队的比赛中去拿苏打水，让他错过了一个关键的投篮；在电影院里大声说话让他感到尴尬；把她的东西搬进他的公寓，送给他一个 蕨类植物象征着他们的关系，甚至带他去看席琳·迪翁 (Celine Dion) 的音乐会，而不是预期的纽约尼克斯队篮球比赛。 在这一切之中，安迪偶尔会露出真实的自己，这让本开始对她产生真挚的感情。

安迪对这个项目感到沮丧，她在本的男孩扑克之夜失去了冷静，希望这会成为迫使他与她分手的最后一根稻草。 然而，Ben 的朋友 Tony 和 Thayer 敦促他向 Andie 寻求夫妻咨询而不是放弃。 安迪请米歇尔假扮成夫妻治疗师，他们暗示本以她为耻。 作为回应，本提议周末将安迪介绍给他在史泰登岛的家人。 在探亲期间，安迪和本建立了真正的联系。
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这对夫妇一起参加公司舞会，菲利普在会上与安迪交谈并告诉本，“我见过她，她爱你，你赢了。” 然而，为了破坏 Ben，Judy 和 Judy 告诉 Tony 和 Thayer，Andie 一直都知道这个赌注，并且正在配合帮助 Ben 获胜。 Tony 和 Thayer 恳求 Andie 保持安静，在不知不觉中向她透露了赌注。 同时，不知道本参与其中的安迪的老板拉娜与他分享了安迪题为“如何在 10 天内失去一个人”的文章的详细信息。 得知本的赌注后，安迪试图在派对上的每个人面前羞辱他，导致一场激烈的争吵，随后他们在舞台上分手。

后来，托尼给本看了安迪写的文章，她承认自己“失去了我唯一爱过的人”。 当发现安迪因为拉娜拒绝让她写严肃的话题而辞去了她在 Composure 的工作，并且她正在前往华盛顿特区接受采访的路上时，本追上了她的出租车并拦住了她。 他指责她逃跑，但他们都流露了彼此的真实感情。 本指示出租车司机将安迪的物品归还给她，因为他将和她一起去，他们分享了一个热情的吻。
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