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At its heart, this is a case fraught with pain and loss that is not unique to this particular period in frontier Kentucky. Although the presence of the Shakers, and a community’s reaction to them, imbue this case with meaning historically, this divorce also speaks to unchanging questions about the nature of conjugal relation in the face of an uncertain eternity. This is a case that reveals something about broader anti-Shakerism, but it also demonstrates that for many, the broader contexts of religious change and budding institutions were not perceptible factors in their experience of life on the frontier. With the following microhistory, the goal is double: both to deepen the understanding of the broader forces at work behind the Bolers’ divorce, but also to restore the lived experience of an intimate conflict amidst uncertainty.