This paper examines aspects of the flâneur and expressions of loneliness that are found within my artistic practice. It expounds on a more contemporary version of the flâneur without gender or class biases and relates this character’s habits to the technique and conceptual framework of paintings that I create. As I walk to and from set destinations throughout the day, I take photo-documentation of quiet, architectural spaces found within the Portland landscape. In translating these images onto canvas, I provide the viewer with perspectives of the isolated dreamer.