Quantum Leap S05E12 - A Tale of Two Sweeties - February 25, 1958

As a horse-playing, traveling brush salesman, Sam finds himself with two wives and two families. Although Ziggy predicts that Sam's mission is to choose between the two lives, the choice is made more difficult by the fact that there's only a 50/50 chance that he'll choose the right one. As if things weren't bad enough, Sam finds that his penniless host owes a pair of bookies some big bucks.