Soon, he throws thousands of women into mourning when he announces on the air that he is getting married. It looks like the infamous charmer is finally met his match. There is one glitch.

Three weeks later, Max is confronted with a vision of his future: love, marriage, kids...death. This is the last woman he is ever going to sleep with. Desperately trying to discover how he can know if he has met the right woman before she wreaks havoc on a major portion of his life, he turns to his best friend, Jay Murphy (Jason Lee). "What if Sam isn't The One after all," he wails. What if she is the first woman who could actually dump Max Abbitt?

Max pleads for Jay to help him find out by testing Sam to see if she would cheat on him. But as Max pursues his scheme, he brings about the very mishaps and miscommunication that will finally make his self-absorbed heart unfold.