When Eric drops out of college and lucks into a job with a small-town newspaper, he meets Anna, an older woman with a story that will both haunt and inspire him for the rest of his life. Set in a remote North Dakota community in the last days before the Internet, the story unfolds around a romance that almost was and a meditation on what constitutes a life well-lived. Narrated by Eric as he looks back on their days together, he struggles to reconcile his memories with what he has since learned about Anna. The Winter in Anna is filled with moments of tenderness, even as it slowly reveals an unbearable tragedy at the heart of a quietly defiant life.