Modigliani's affair with Hastings, with whom he had been living since 1914, was already ending by 1915, a year the artist's biographers treat as a turning point in his development^[1]. It was in this same period that his friendship with Picasso broke down after a disagreement whose cause remains unrecorded, and that Modigliani began moving away from the sculptural preoccupations of the previous years towards the sustained run of paintings that would occupy him until his death^[1]. Hastings, for her part, was an established figure in her own right: a South African-born writer and critic active in London literary circles before and during her time in Paris.

Modigliani's Montparnasse years were marked by heavy drinking, poverty and a physical constitution already weakened by childhood illness. Contemporary and later accounts describe nights spent drinking cheap wine and absinthe and smoking hashish, portraits sold for a few francs to fund the next round, and a temperament that alternated between exuberance and violence^[2]. He caught the pneumonia that killed him after a night of drinking in the cold, dying in Paris in January 1920 at thirty-five^[2]. The Hastings relationship sat inside this same stretch of his life, and the sequence of portraits he made of her, more than a dozen sittings by most counts, is unusual even within an oeuvre built mostly on quick, single-session studies of the people around him.