This chapter looks at the role that marriage (to a woman) played within the lives of trans men. We start with the biography of James William Hathaway (Ethel Kimball), born in 1882, whose life history primarily seems to be one of lawbreaking, with gender a minor note in the tune. While living as a woman in her twenties, she was arrested for forgery and then again for using the excuse of test driving an automobile to go on a joy-ride with a group of female friends. At one point during this general period she married a man.