Quantum Leap (1989)

S05E12 A Tale of Two Sweeties

On February 25, 1958, Sam, a playful traveling brush salesman, unexpectedly juggles two wives and two families. Ziggy suggests that Sam's task is to decide which life to embrace, but the dilemma becomes even more complicated with only a 50/50 chance of making the right choice. To complicate matters further, Sam discovers that his broke host is deep in debt to some dangerous bookies.