Joy Hester holds an important place in Australian art history. Hester was a founding member of the Contemporary Art Society, which was of critical importance in Australia's modern art movement. She worked within a circle of artists, mentored by John and Sunday Reed at Heide. Hester's work has been widely exhibited and the subject of numerous publications, catalogues and is included in national, state, regional and university art collections.

Hester completed two series of works on the theme of love - the Love series (1949) and the Lovers series (1955-56). While Lovers with Rose has been dated c. 1947, Janine Burke noted that Hester rarely dated her works and dating has therefore always been approximated based on stylistic evolutions or the recollections of friends and family.

The year 1947 was a pivotal one for Hester who both left her first husband, the artist Albert Tucker, for the artist and poet, Gray Smith, and discovered she had Hodgkin's Disease, which led to her premature death thirteen years later. While the male figure in Lovers with Rose is assuredly Smith, Hester frequently used his likeness to express particular psychological or emotional states and not necessarily as a literal portrait. However, when Hester began the Love series in 1949, it '...introduced a new level of poetic intimacy that was directly associated with her love for Gray Smith.'

Hester is also known for drawing prominent, almost hypnotic, primitive eyes. In fact, she said in relation to the stalk eyes she depicted around 1945 that the eyes were the most important starting point for her and in 1947, Hester began her Faces series, which focused particularly on the subjects' eyes.

Around August 1947, Hester wrote to Sunday Reed, 'How can I love Gray when he is me...He is the 'man' of me and I am the 'woman' of him...part man, part woman...It's like a puzzle piecing oneself together.'

After Hester left Tucker, the new couple lived for a while in Rose Bay, Sydney.