在大学期间，莱拉（安娜·帕奎因 Anna Paquin 饰）和劳拉（凯蒂·霍尔姆斯 Katie Holmes 饰）是一对无话不谈的好友兼室友，而如今，劳拉即将和大学同学汤姆（乔什·杜哈明 Josh Duhamel 饰）踏入婚姻的殿堂，身为死党的莱拉怎能不出手相助？于是，伴娘这一光荣的身份便降临到了莱拉的肩膀上。
可是对于连男友都没有的莱拉来说，目前的处境让她十分的尴尬，不仅仅是因为自己单身的状态和曾经暗恋过汤姆的事实，还因为即使是现在，她还对新郎汤姆恋恋不忘。对于莱拉的尴尬，沉浸在幸福之中的劳拉并未察觉，而随着婚期的将近，莱拉感觉自己变成了一个正在倒计时的定时炸弹，即将爆发。

Sparks fly when self-sufficient single mother Abigail meets magnetic perennial bachelor Ben. On their first date, they collaborate -- in jest -- on the ultimate list: 10 things to do together before they break up. But when fate intervenes, they soon embark on the most challenging journey of all -- building a family together, and the chance to trade their cynicism for hope.

When talented young writer Elizabeth Wurtzel earns a scholarship to Harvard, she sees it as her chance to escape the pressures of her working-class background and concentrate on her true talent. But what starts out so promising leads to self-destructive behavior and paralyzing depression that reflects an entire generation's struggle to navigate the effects of divorce, drugs, sex, and high expectations.