After more than three decades of teaching English in Chicago schools, Robert Jones is retiring early. He begins a food delivery job. He enjoys the encounters with customers from many different walks of life, as well as the solitude of driving alone most of the day. One evening, he has an undeliverable food package when a customer can't be found. He chooses not to eat it or dispose of it, as his employer suggests. Instead, he stops at a train's underpass in Chicago's Little Village where he has previously seen homeless people gathered, and he offers the food to them. There, he meets several people, including a transient woman named Berta. Though Berta is allegedly a lady of the evening with an admitted drug addiction, Robert takes a great liking to her, and their unlikely companionship develops. Telling a family member about having befriended a homeless woman and some of her acquaintances on the street, Robert is encouraged to write about his adventures. Soon after, he begins writing his novel. While attempting to become an acclaimed author by writing his more-truth-than-fiction story about the street people he has met, an interested publisher insists that Robert add spicy scenes, which is something Robert is very reluctant to do. "Robert's Unexpected Friendship" is a contemporary urban drama about unlikely companionship, urban street life, family, and an author's ethical dilemma.
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