Looking at this painting, a rare quote by the artist and the insight of art critic Robert Ayre cited below leads the viewer to speculate on various interpretations of the work.

“In many of my pictures there is a man walking by himself, that man is always me,”[1] metaphorically Philip Surrey said. Remarking at the lone figure just off centre in the middle ground one might speculate this to be Surrey as the spectator to the scene unfolding.

“The city is his place. Night is his time, and the overwhelming solitude of man his theme.... Apprehension and fear lurk in the threatening shadows, but the greatest terror is loneliness.” [2] Robert Ayre wrote about Philip Surrey. The notions of “fear” and “apprehension” and other tensions are expressed in many ways in his paintings. Certainly, there is a tension in the relationship of the leggy maxi-coated young lady with the red tuqued fellow seen only from the back.
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Footnotes:
[1] Margaret Surrey, Biographical notes of Philip Surrey, Philip and Margaret Day Fonds, P85A, National Archives of Canada, Estate Philip Surrey.
[2] Robert Ayre, City and the dream of Philip Surrey, Canadian Art, Vol. 21, September 1964, p. 287