Rogers' sales catalogue describes this group as follows: "A Puritan Elder is riding home from Sabbath meeting. He has dropped the reins on the horse's neck and has been absorbed in studying his Bible. His daughter rides behind him on a pillion, while a young man walks by her side and offers her an apple from amongst the hatful he has gathered. This is considered a desecration of the Sabbath by the stern father, who looks at the young man reprovingly." At the apex of the composition is the Elder, sitting ramrod straight in the saddle. He glowers forbiddingly as he turns his head toward the young man handing an apple to his daughter. Their curving postures contrast with his stiff bearing. Their hands touch fleetingly, and their shared gaze parallels the older man's glare, which the young lovers barely notice. Rogers rendered the figures in simple Puritan dress. The two men wear high, wide-brimmed hats, though the Elder's is firmly placed on his head, enhancing his intimidating height, while the younger has taken his off to use as an apple basket-in perhaps another breach of decorum. Rogers was acclaimed for his mastery of equine anatomy, and the horse bearing the Elder and his daughter has a part in the story as well, pawing the ground as if impatient to be on its way. In this work the artist returned to the tried-and-true subject of courtship that he had used to great effect in Parting Promise (1929.82, 1940.203) and The Tap on the Window (1929.86), among other groups. However, this time he also satirized the nation's Pilgrim roots. The last quarter of the nineteenth century witnessed a revival of interest in the country's origins, inspired by the 1876 centennial celebrations and by nativist fears that massive immigration might dilute American culture. Some artists responded by heroizing the early settlers, as in the case of John Quincy Adams Ward's life-size bronze The Pilgrim, commissioned in 1885 by the New England Society in the City of New York and installed in Central Park. Rogers took the opposite approach, skewering notions of the country's mythologized Puritan roots by gently mocking their strict codes of conduct. The Elder is a caricature of righteous indignation over a minor infraction of the code of Sabbath rest, and his consternation can only be exacerbated by the deleterious influence the supposedly wayward young man might have on his daughter. One writer chuckled, "one almost hears the uncorking of Puritanical vials of wrath." When Rogers created this sculpture, he was probably aware of contentious debates over another question of Sabbath rest, not least, whether cultural institutions such as the Metropolitan Museum of Art should open on Sundays to allow working people to attend. Here Rogers seems to have registered his opinion that such restrictions need not be taken to extremes. Newspapers often connected The Elder's Daughter with "Why Don't You Speak for Yourself, John?" (1936.660, 1926.36, 1958.14a) from the previous year, another scene of flirtation from the nation's early history, taken from Henry Wadsworth Longfellow's poem The Courtship of Miles Standish. The New Orleans Daily Picayune announced, "John Rogers Sculpturing Puritans Again," and other newspapers paired the two groups by illustrating them side by side. In the 1885 group Rogers took his inspiration from an already existing story, but in The Elder's Daughter his original conception suggests not only the wellspring of humor from which his subjects flowed but also a hint of mischievous irreverence rarely seen in his work.

The subject was the youngest of seven children of Kiliaen and Olivia (Atterbury) Van Rensselaer. He graduated from Yale in 1908 and attended New York Law School. He entered the diplomatic service as clerk of the Americam embassy in Lisbon, and from 1915 to 1917 he was third secretary of the American legation in Rome. His portrait was a gift to the Society from his brother.