Anne Rutledgewas the daughter of the owner of an inn at New Salem which Lincoln was a postmaster and resided in occasionally.  David Herbert Donaldson described Rutledge as "fair skin, blue eyes, and auburn hair.  Only five feet, three inches between one hundred and twenty and one hundred and thirty pounds.  Rutledge was engaged to John McNamar, but in 1835 Lincoln and Rutledge's friendship grew into romantic relationships.  Lincoln described her as "Pure and kind a heart as an angel, full of love, kindness, and sympathy."  Lincoln and Rutledge spoke of marriage, but Lincoln had no career.  He was pursuing a legal career and Rutledge was still engaged to McNamar so they decided to wait a year to wed until his career was settled and her engagement was over.

    On August 25, 1835, Ann suffered from a brain fever and died.  Abraham was the last person she saw and spoke to before her death.  AFter his brother Thomas, sister Sarah, his mother's, and now Ann's death Lincoln showed his first visible case of depression.                              

Mary Toddwas a wealthy and highly educated woman from Kentucky.  Unlike Lincoln, Mary was very social.  This actually helped their relationship because she kept the conversations going and found Lincoln's shyness attractive.  The two made a perfect couple.  They were both Kentuckians, loved poetry (most specifically Robert Burns), and they both were Whigs who followed Henry Clay.  During Lincoln's political career his biggest competition was STephen Douglas.  Just like in politics, Douglas and LIncoln competed for Mary.  Mary went out with Douglas a few times, but eventually Lincoln won out because Douglas's political career was more important to him that getting into a relationship was.  In 1840, Mary and Abraham got engaged, but similar to the Mary Owens story, Lincoln got cold feet and ended the engagement.  And like Mary Owens, Lincoln realized he loved her.  He lied in bed for "over a month and was only strong enough to speak louder than a whisper," as Herndon described it.  Mary and Abraham's relationship began to rebuild in 1842 when a column written by the two  was published in the Sangamo Journal.  The article was about the political decisions involving banks by Democratic State Auditor James Shields.  This article found Lincoln in a lot of trouble.  Shields challenged him to a duel with broadswords.  The duel was to be fought in Ohio because Illinois outlawed duels, but fortunately the duel was never fought.  What it did do however was reunite the relationship of Abraham Lincoln and Mary Todd.

    It is speculated that the two wed as a result of her being pregnant, but regardless they did wed.  After marriage, Mary and Abraham first lived in a one room apartment at Globe Tavern.  They each cared very much for each other, but marriage as a whole was troublesome. Both Abraham and Mary suffered from some sort of depression and it led to a lot of bickering.  Abraham called Mary "puss," "little woman," and mother."  Mary called him "Mr. Lincoln."  Mary was lively, talkative, and sociable.  Lincoln was slow and moody.  Mary slaved around the house, while Lincoln was a bum.  In 1847, Lincoln was elected to congress so the family moved to Washington D.C.  In 1854, Lincoln retired from politics and got back into the law circuit.  Three months out of the year Lincoln would be away on the circuit.  He did not provide the warmth and comfort that Mary craved.  Regardless,  both remained loyal to each other until the day Lincoln died.