It was also during the New Salem years that Lincoln's first associations with women are recorded. The best known was his relationship with Ann Rutledge. While there are variations, the core of the story consists of the following: Lincoln and Rutledge became romantically involved sometime after Ann's fiancée, a Mr. McNamara, went back east to tend to family business. In the summer of 1835, nearly three years after McNamara's departure, Ann died of what was referred to as a "brain fever," either typhoid or malaria. The degree of Lincoln's grief following Ann's death is debated and ranges from his wanting to be buried with her, to stating that his heart is buried with her, to feeling sad at the loss of a friend.

Another, better documented, romance of Lincoln's during this time was his relationship with Mary Owens. Lincoln proposed to Owens in the fall of 1837, but much to his relief she turned him down. She later recalled that "Mr. Lincoln was deficient in those little links which make up the great chain of womans happiness."

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