The painting was mentioned in the Pio da Carpi inventory of 1624. Traditional literature, on the other hand, placed it in the collection of Cardinal Ludovico Ludovisi (1595–1632), which was dispersed in 1660 by his brother Niccolò, the Prince of Piombino, in whose inventory of 1633 it appeared as a work by Castelfranco’s maestro.
In 1734, it was in Ferrara, in the collection of Cardinal Tommaso Ruffo, where it was attributed to Dosso Dossi. Following the donation by Prince Fabrizio Ruffo di Motta Bagnara in 1919, the work entered the Museo del Palazzo di Venezia.
More recently, on the other hand, Rognoni (1990) ascribed the work to the circle of Giorgione, against the opinion of Lucco (1980, 1990), convinced that it was indeed by the Venetian master, as was Ballarin, whose various publications (1976–78 and 1993) forcibly asserted the name of Giorgione, dating the picture to about 1502, in the period of such masterpieces as the Portrait of a Man in Armour and The Tempest. The scholar has focused on the cultural matrix of the painting, which has its roots in the courtly romances and Neoplatonic Venetian literature of the early Cinquecento as typified by Pietro Bembo’s Asolani.
The painting provides an original interpretation of the two-figure portrait, concentrating on the subject of amorous passion leading to melancholy love.