Ann Rutledge was the daughter of one of the founders of New Salem, James Rutledge, and was eighteen years old when Abraham Lincoln arrived in 1831. Accounted the prettiest girl in the village, she had already had, by this time, a number of suitors. Some descriptions of her, like that of William G. Greene, seem extravagant: “This young lady was a woman of Exquisite beauty, but her intellect was quick -- Sharp -- deep & philosophic as well as brilliant. She had a gentle & kind a heart as an angl -- full of love -- kindless -- sympathy. She was beloved by evry body and evry boody respected and lovd her -- so sweet & angelic was she. Her Character was more than good: it was positively noted throughout the County.”4 Other descriptions, such as James Short’s, are more moderate: “Miss R was a good looking, smart, lively girl, a good house keeper, with a moderate education, and without any of the so called accomplishments.”5 But there was wide agreement that Ann Rutledge was bright, attractive, kindly, and well liked.
Lincoln seems to have admired the young woman who combined these qualities from an early date. Jason Duncan, who came to New Salem at the same time as Lincoln, wrote Herndon: “he [Lincoln] was verry reserved toward the opposite sex. while I lived and boarded in the same place with him, do not recollect of his ever paying his addresses to any young lady though I Know he had great partialities for Miss Ann Rutlege, but at that time there was an insurmountable barrier in the way of his ambition.”6 Duncan, who left New Salem in 1833, is describing the state of affairs he knew at first hand and is referring to Ann’s engagement to a man named John McNeil, which must have occurred within a few months of Lincoln’s arrival.7 According to her family, she had been courted by both partners of the mercantile firm of Hill and McNeil, not knowing that the latter’s name was really McNamar. Her brother Robert told Herndon: “Samuel Hill first courted Ann, she declined his proposition to marry, after which, McNamar paid his addresses, Resulting in an engagement to marry.”8I also liked that this covered the "legend" that tends to overshadow the truth:
In legend, Ann is always the tavernkeeper’s daughter and Lincoln the love-struck boarder, and while they probably became acquainted when he was staying at the tavern during his first year in the village, she was promised to another at that time, and her courtship with Lincoln was actually carried on at least two years later. By this time she was living on a farm with her family in the Sandridge neighborhood, several miles north of New Salem. Almost no details of this courtship have come down to us, and a large part of the reason surely has to do with the unusual circumstances just described. As far as her friends and neighbors were aware, Ann was publicly engaged to John McNeil, or McNamar, and very few outside the family knew differently. James Short, who lived near the Rutledge family at Sandridge, told Herndon: “Mr L. came over to see me & them every day or two. I did not know of any engagement or tender passages between Mr L and Miss R at the time; but after her death, which happened in 34 or 35, he seemed to be so much affected and greived so hardly that I then supposed there must have been something of the kind.”13 Here Short is acknowledging that he knew Lincoln visited the Rutledge farm every few days but didn’t realize at the time that there was a courtship in progress. Though a majority of Herndon’s two dozen informants giving testimony about the Ann Rutledge affair affirmed the existence of an engagement between Lincoln and Ann, most of them, like Short, probably learned about it after the fact.
Ann’s reluctance to become publicly engaged to Lincoln while still betrothed to another man suggested to Herndon (and many others since) that perhaps she and Lincoln were never actually engaged. But her family, whose spokesman was Ann’s brother Robert, insisted otherwise: “after McNamar left Menard Co. to visit his parents and during his prolonged absence, Mr Lincoln courted Ann, resulting in a second engagement, not conditional as my language would seem to indicate but absolute, She however in the conversation referred to by me, between her & David Rutledge urged the propriety of seeing McNamar, inform him of the change in her feelings & seek an honorable releas, before consumating the engagement with Mr L. by Marriage.”14 In other words, Ann felt justified in becoming engaged to Lincoln but thought, contrary to her brother David, that she owed McNamar an explanation before actually being married.
Ann dies before this can go any further and the author gives some evidence that Ann may have had emotional problems that added to the typhoid that killed her: