What do you do if you're about to get married and you've got cold feet? If you're Max Abbitt, you ask your best friend Jay (Jason Lee) to sleep with your fiancée. Max, a sportscaster dedicated to playing the field, and the beautiful, intelligent Samantha Andrews are a mismatch made in heaven. Jay, who recently had his heart broken, couldn't be unhappier for them. Before he knows it, Max is giving up swinging singlehood, but the thought of one woman for the rest of his life suddenly throws Max into a panic. Max reasons that if Samantha cheats on him first, he'll be off the hook. When he asks Jay to help him "test" the relationship, not only does Jay think Max is deranged, but Jay wants nothing to do with the scheme. Unfortunately, a little compromising finds Jay and Samantha and Max in an awkward position.