Although considered apocryphal by many, Lincoln's early romance with Ann Rutledge has entered the annals of American folklore. Rutledge was born in Kentucky in 1813 and moved to Illinois at the age of sixteen. The Rutledges were among the founding families of New Salem, and they set up a tavern in the town. Lincoln boarded with them for a short time upon arriving in New Salem. Additionally, he and Ann were classmates under the tutelage of Mentor Graham, the local schoolmaster. Despite their affinities, Ann became engaged to another man, who subsequently abandoned her.
Many have speculated that Lincoln and Rutledge were unofficially engaged thereafter, on the understanding that they would be free to marry after Lincoln obtained a measure of standing in the legal profession. But in the summer of 1835, Rutledge fell ill, probably with typhoid fever. As she lay dying, Lincoln made a final private visit to her. In later life, Lincoln visited her gravesite frequently. The periods of melancholy to which he was so prone throughout his life may well stem from this early trauma. In confidence, right up until his death, Lincoln would reveal her continuing presence in his memories and thoughts.
After Lincoln's death, the story of Ann Rutledge became something of a cause celebre. Right up to her dying day, Lincoln's wife Mary Todd Lincoln vehemently denied the whole affair. However, in 1866 Lincoln's longtime law partner William H. Herndon conducted an exhaustive series of interviews among former residents of New Salem to prove the veracity of the story. Among the many who participated in the interviews, Mentor Graham himself went on record to reveal the unofficial engagement between Lincoln and Rutledge, recalling that Lincoln had contemplated suicide in the aftermath of Rutledge's death. Even in the face of this evidence, naysayers continue to deny that any romantic relationship existed between Lincoln and Rutledge, pointing to Herndon's bitter hatred for Mary Todd Lincoln, and thus a hidden agenda in his pursuit and presentation of the matter.
In any event, Lincoln, though much affected by Rutledge's death, eventually composed himself and began to court again. In 1836, on the rebound and somewhat off the cuff, he proposed marriage to Mary Owens, a largish 28-year-old Kentucky woman visiting her sister in New Salem. However, Lincoln continued to be plagued by sporadic bouts of depression, which perhaps diminished him in Owens's eyes. When he proposed marriage in the summer of 1837, she turned him down, remarking in a letter that he lacked "those little links which make up the chain of a woman's happiness."
After this failed courtship, Lincoln moved to Springfield for legal, political, and perhaps social reasons. But Lincoln's first months in Springfield were by no means a social success. On account of his gangly carriage and rough manners, he found himself somewhat out of place in the more polished circles he tended increasingly to frequent. It wasn't until the end of 1839, well into his thirtieth year, that Lincoln met his future wife at a Springfield dance. Mary Todd, a twenty-one-year-old belle from a distinguished Kentucky family, had recently arrived in the Illinois state capital to stay with her older sister Elizabeth and brother in-law Ninian Edwards. Lincoln was drawn to her at once, and they became engaged in less than a year.
From the beginning, the engagement was a troubled one. The Edwards and Todd families disapproved of the courtship, considering Lincoln a country bumpkin unfit for the grace of Mary's hand. With a lack of support for the relationship, and burdened additionally with doubts of his own, Lincoln broke off the engagement with Mary Todd on New Year's Day, 1841. More than eighteen months would pass before their reconciliation, a period in which Lincoln engaged in some reckless and unprecedented behavior.