The painting we present today is a great example of Dante Gabriel Rossetti's mature work. Rossetti, both a poet and a painter, was inspired by the stories from the Bible, Greek mythology, and Dante's and Shakespeare's writings. His works are filled with Romantic poetic sensibility that features images of the femme fatale. Rossetti, also known for his lively relationships with women, used his women friends and lovers as models. The model for this painting is Alexa Wilding, who frequently appeared in Rossetti's works from the spring of 1865 onwards.
A beautiful young woman with richly braided long brown hair and wrapped in a deep red robe raises a golden cup to her lips as she holds the cup's lid to her breast with her left hand and faces the viewer with a dream-like expression. This cup, which gives the work its name, is a cup from which close friends and especially lovers both drink. Here the cup is suitably embellished with heart-shaped designs. The frame of this work is inscribed "Douce nuit et joyeux jour/ A chevalier de bel amour (Sweet night and pleasant day/to the beautifully loved knight)." This inscription shows that the image probably represents a toast to the woman's knight, who is leaving for war or has left for war. While the source of this quote is uncertain, it is thought that Rossetti, steeped in Arthurian legend, wrote the poem himself. Ivy, the symbol of fidelity, is also present, and the shape of its leaves is reflected in the heart-shaped designs on the loving cup.