Sherman's March (1986)

Documentarian Ross McElwee originally set out to make a travelogue of sorts tracing General William T. Sherman's infamous scorched-earth march through the Confederacy in the latter stages of the Civil War. Instead, haunted by a recent breakup with a girlfriend, McElwee ends up documenting his progress -- or lack thereof -- in starting a new relationship. His journey then becomes one of self-reflection and self-discovery rather than a historical/sociological exploration.