Your question immediately brings to mind a series of paintings created by Lucas Cranach the Elder in the 16th century. The title of one his works is similar to the wording of your question, namely "Old Man and Young Woman". The pairing of an old person with a younger person of the opposite sex is a subject that recurs in several of Cranach's paintings. You can find a few of them listed in the Web Gallery of Art if you look at its page of Cranach's miscellaneous paintings. There you will see pairings of older men with younger females, as well as an old woman with a younger male. Cranach portrayed the older subjects in these photos as though they are in love with the younger subjects, and their German titles imply that the focus of these paintings is on the amorous feelings of the older person rather than on an equitable relationship. For example the title "Der verliebte Alte" (there are more than one of his paintings with this title) translates to "The old man in love", and "Die verliebte Alte" translates to "The old woman in love". In each of the paintings of this type, Cranach gives the older person a lustful expression and shows the younger person looking away with less-than-adoring expressions rather than making eye contact.
Another place to find a collection of images of Cranach's "ill-matched pairs" is online at the Cranach Digital Archive. You can filter by "Subject" and then the sub-category of "Genre", and then select "An Ill-matched Pair". There are nineteen of his old-and-young paintings there. You can hover your cursor over them to enlarge the image and also view each painting's date of creation and the name of the places in which each one is currently housed.
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