The pairing of unequal couples has a literary history dating back to antiquity when Plautus, a Roman comic poet from the 3rd–century BC, cautioned elderly men against courting younger ladies. By the late–15th and early–16th centuries, the coupling of old men with young women or old women with young men had become popular themes in northern European art and literature.
This painting provides a clear illustration of the ideas that old age, especially lecherous old age, leads to foolishness—with the fool participating in the deception by helping to rob the old man's purse—and that women's sexual powers cause men to behave absurdly and to lose their wits and their money. The deck of cards may allude to competition between the sexes, morally loose or amorous behavior, and the loss and gain of money through gambling.
The painting is an example of Massys' ability to assimilate elements from both northern and Italian art. Apparently familiar with Leonardo da Vinci's grotesque drawings of physiognomy and distortion, Massys adapted the facial type for the old lecher from one of Leonardo's caricatures, and the complicated pose of the suitor from Leonardo's lost drawing of an ill–matched pair, known today through a later copy.
More information on this painting can be found in the Gallery publication Early Netherlandish Painting, which is available as a free PDF https://www.nga.gov/content/dam/ngaweb/research/publications/pdfs/early-netherlandish-painting.pdf