Privileged teenage friends Jenny, Nell and Stream spend their senior year on a quest to rid Stream of her virginity. However, Stream wants more than just her first sexual experience. She wants to have an orgasm -- but achieving this proves problematic, as the boys she meets are hardly sensitive enough to provide her the release she seeks. When it becomes clear that Nell and Jenny have never experienced an orgasm either, all three set out to get one.

海伦（凯特·卡普肖 Kate Capshaw 饰）早年间和丈夫离了婚，带着女儿开了一间书店。如今已经42岁的她早就看淡了人生中的风风雨雨，心如止水。在海伦的身边，还是有着不少的追求者。乔治（汤姆·塞立克 Tom Selleck 饰）和海伦曾经是同学，他一直爱慕着海伦，但他选择将这份感情埋藏在心底，同另一个女人结婚了。乔尼（汤姆·艾弗瑞特·斯科特 Tom Everett Scott 饰）是在书店里打工的雇员，虽然他已经有了女友珍妮弗（朱丽安妮·尼科尔森 Julianne Nicholson 饰），但还是难以抵挡哈伦散发的魅力。
一天，海伦在书店里见到了一封行文热烈的情书，这封情书没有署名，在这个小镇上，很多人的命运因为这封情书改变了。