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At the end of the 20th Century, a series of letters written during the early 1930's are discovered on opposite ends of the United States. In Los Angeles, Charlie is stumbling through life trying to find a shred of happiness and a clue as to who he really is. His next door neighbor loans Charlie some letters written by Ruby Jean Demonde; a lonely blues singer living in Harlem during the great depression. As Charlie sets out on an adventure to learn more about Ruby Jean's life, he ends up discovering more about his own. While in New York, Simon, a workaholic stock trader doesn't realize his own family relationships are slipping away. When his mother falls ill, Simon goes home to Pennsylvania and soon finds a detailed account of his grandparents' courtship through a series of letters hidden away in the attic. What can a pair of young lovers in Western Pennsylvania, a blues singer in Harlem, and an undertaker in Galveston, Texas possibly have in common? In The Most Unusual Correspondence, Charlie and Simon find out some of us are simply connected by words on a page.