Awaiting execution, Denver Bayliss gains an unlikely friend and confidant in Fred Whitmore, a former cop who is now a prison guard. Whitmore's life is a mess, however: he shuts out his wife and can't relate to his son. As Bayliss' execution draws nearer, Whitmore clashes more and more with Lt. McMannis, his supervisor, over Bayliss' treatment. Bayliss gives Whitmore a new understanding of life by helping him come to terms with a traumatic past, and Whitmore helps Bayliss to make his peace with himself and the world.

亨利·罗斯（亚当·桑德勒）是个典型的花花公子，他最擅长的事就是以不同的身份，让美女迷恋上他，并在事后，迅速从关系中脱身。身为夏威夷海洋馆的兽医，亨利有着无尽的浪漫情怀来感染到此休闲的美女，这一次他看上了在餐馆独自用餐的露西(德鲁·巴里摩尔饰)。
他们在一起谈天说地，用百吉饼搭建小房子，笑声不断。亨利对女孩恋恋不舍，相约明晨再次一起用餐。然而，第二天清晨，当亨利热情的与露西打招呼时，露西却宛如陌生人一般冷淡。原来女孩由于车祸患上了奇怪的短期记忆丧失症，记忆永远停留在车祸的前一天。
情圣亨利遇到了自己的难题，他坠入的情网，却爱上一个不断对爱情失忆的女孩儿……