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Hi Will,
I share your love for architecture and I liked your idea of placing the girl in the window. However, the angle of the window and the stern look on the girls face make the painting reminiscent of something one would see as a book illustration, rather than a traditional portrait. If your intention is to tell a story then the image works, but as a portrait it is unsettling.
If you are planning to rework the image my first recommendation would be to do some sketches to work out the composition. If you keep the angle of the window, I would have the girl look down with a friendlier expression. Or change the angle so it is level with the viewer.
If you read about the pope's picture on SOG, you will notice that the angle in which the sitter is depicted conveys a certain message to the viewer. Decide what that message is and change position and expression of the girl accordingly.
Have fun experimenting with different angles!
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