When Alf reveals to his best friend, Jim, that his long-term relationship had ended, it sparks up an animated discussion about a mutual friend of theirs, Will, a reputed Lothario perpetually living up the bachelor lifestyle. According to Alf, Will is a changed man, and going steady, but Jim begs to defer, convinced he will slip back into his wicked ways, given half the chance. Both are adamant they are right, so they agree on a wager, and set him up with an escort to see which way the pendulum swings.