Abraham Lincoln raked his boney fingers through his unruly hair as he hunched over the desk. Before him, under a flickering lantern, rested a piece of paper that could define his entire life. The scrawl of his writing on the page flicked up and down upon the lines as if they were musical notes. But the song they sang was one that worried Lincoln. This was a letter of freedom–one that would liberate souls.
But this wasn’t the Emancipation Proclamation. The year was 1837 and the person being freed was Lincoln himself from a bad relationship. This was Abraham Lincoln’s ultimate breakup letter!
Ever since Lincoln was elected in 1860, people have obsessed over finding the secret to what made Lincoln…well…Lincoln. Everything from digging up the most obscure letters and pouring over them word for word to anachronistically applying modern labels like “clinically depressed” to him has been tried. Some have even wondered if Lincoln was gay! 
All of this is to say that Lincoln’s love life has fascinated readers for generations!
But did you know that before Lincoln had met his future wife, Mary Todd, he was practically engaged to another woman by the name of Mary Owens?
In the early 1830s, Lincoln lived in New Salem, Illinois and met Mary when she was in town from Kentucky to visit her sister. By 1837 Lincoln had moved to Springfield and the sister offered to match Lincoln and Mary if she could bring her back to the state. Lincoln half-jokingly agreed, as he remembered that he had “thought her inteligent [sic] and agreeable, and saw no good objection to plodding life through hand in hand with her.” As you can see by his totally-excited-and-definitely-not-lukewarm words, Lincoln was thrilled at the idea of “plodding” through life with Mary…
Before Mary came back to Illinois, they wrote letters to each other and Lincoln did his best to make life in Springfield seem as unappealing as possible to his potential fiance. “The thing of living in Springfield is rather a dull business,” Lincoln wrote to Mary. “I am afraid you would not be satisfied. There is a great deal of flourishing about in carriages here, which it would be your doom to see without shareing [sic] in it. You would have to be poor without the means of hiding your poverty.”
So Springfield was boring, yet people were “flourishing about” in their carriages? Lincoln clearly hadn’t mastered the art of persuasion yet…
When Mary returned that year, Lincoln realized he was in a pickle. He tried to put off meeting with her again and again for as long as possible. Several days passed and when he finally had to meet her again, he immediately regretted everything–expressing his reaction in a later letter to a friend:
I knew she was over-size, but she now appeared a fair match for Falstaff; I knew she was called an ‘old maid’, and I felt no doubt of the truth of at least half of the appelation…when I beheld her, I could not for my life avoid thinking of my mother; and this, not from withered features, for her skin was too full of fat to permit its contracting in to wrinkles; but from her want of teeth…
Yes, letters like this show that Lincoln wasn’t the perfect, kind saint he’s often made up to be, but I think it also shows how elaborate and brutal 19th century insults were!
“But what could I do?” Lincoln asked his friend. “I had told her sister that I would take her for better or for worse; and I made a point of honor and conscience in all things, to stick to my word.” He tried to convince himself that he could love her–writing about how he focused on how smart she was–but nothing worked. When he could not longer “procrastinate the evil day,” Lincoln proposed…and got rejected!
Lincoln was shocked. “At first I supposed she did it through an affection of modesty…but on my renewal of the charge, I found she repeled [sic] it with greater firmness than before.”
So Lincoln not only got rejected once, but got rejected several times until he “was finally forced to give it up, at which I verry [sic] unexpectedly found myself mortified almost beyond my endurance.” Lincoln was never a self-obsessed man or thought he was particularly handsome, but even he had to admit his “vanity was deeply wounded” when he was rejected by a woman he’d held no interest in. 
In order to make sure their “relationship” was completely finished, Lincoln wrote one final breakup letter to Mary on the same day she left Illinois. He gave the classic we can still be friends lines while ultimately making sure she knew she could really get out of it all. In his awkward, clunky breakup letter, he ended it with, “If it suits you best to not answer this–farewell–a long life and a merry one attend you.”
Mary never responded…
— Sources: —
 C.A. Tripp’s 2006 book, The Intimate World of Abraham Lincoln argues Lincoln was actually gay. Professional historians have essentially debunked that notion fully. First, it’s anachronistic to apply modern terms when the concepts of “gay” and “homosexuality” were completely different to the past. Second, Tripp’s evidence is severely lacking. Tripp focuses on the fact that Lincoln shared a bed with his business partner Joshua Speed. But millions of people shared beds with others of the same sex. Just look at boarding houses of the period. Finally, historians have also said “so what?” While there is no way that Lincoln fits within our modern notion of “gay,” so what if he was?
 Abraham Lincoln to Mrs. Orville H. Browning, April 1, 1839, in Lincoln: Speeches and Writings 1832-1858, ed. Don E. Febrenbacher (New York: Literary Classics of the United States, 1989): 37-38.
 Abraham Lincoln to Mary S. Owens, May 7, 1837, in ibid., 19.
 Abraham Lincoln to Mrs. Orville H. Browning, April 1, 1839, in ibid., 37-39.
 Abraham Lincoln to Mary S. Owens, August 16, 1837, in ibid., 20.