This is vaguely similar to an idea for a painting I've had in my head for a few years now, but haven't attempted because I don't think my skills are up to the task yet. And, funnily enough, I when I first got the idea I thought it would look good in your painterly style.
I discovered a new word the other day, "saudade." It's a Portuguese word that means "a feeling, a longing for something or some event that one is fond of, which is gone, but might return in a distant future. It often carries a fatalist tone and a repressed knowledge that the object of longing might really never return." That's the emotion I wanted to convey in my painting, and the same feeling I get from this one.