A widely held trope regarding Alexander Hamilton is that he actively pursued women left and right. During the American Revolution, the dashing and attractive young man on the rise supposedly earned a reputation as a tomcat. One Hamilton biographer, for instance, remarked that by 1780 Hamilton had already made “a career of dalliance that was at once gallant, predatory and oddly guarded.”
Alexander Hamilton to Catharine “Kitty” Livingston, April 11, 1777
One piece of evidence biographers point to as proof of Alexander Hamilton’s lascivious pursuits is a letter he wrote as a twenty-year-old to twenty-six-year-old Catharine “Kitty” Livingston on April 11, 1777. In this letter, Hamilton wrote:
Though I am perfectly willing to harmonize with your inclination, in this respect, without making the cynical inquiry, whether it proceed from sympathy in the concerns of the public, or merely from female curiosity, yet I will not consent to be limited to any particular subject. I challenge you to meet me in whatever path you dare; and if you have no objection, for variety and amusement, we will even sometimes make excursions in the flowery walks, and roseate bowers of Cupid. You know, I am renowned for gallantry, and shall always be able to entertain you with a choice collection of the prettiest things imaginable. I fancy my knowlege of you affords me a tolerably just idea of your taste, but lest I should be mistaken I shall take it kind, if you will give me such intimations of it, as will remove all doubt, and save me the trouble of finding it out with certainty myself. This will be the more obliging, as, without it, I should have a most arduous task on my hands, at least, if connoisseurs in the sex say true, according to whose representations, contrary to the vulgar opinion, woman is not a simple, but a most complex, intricate and enigmatical being.
After knowing exactly your taste, and whether you are of a romantic, or discreet temper, as to love affairs, I will endeavour to regulate myself by it. If you would choose to be a goddess, and to be worshipped as such, I will torture my imagination for the best arguments, the nature of the case will admit, to prove you so. You shall be one of the graces, or Diana, or Venus, or something surpassing them all. And after your deification, I will cull out of every poet of my acquaintance, the choicest delicacies, they possess, as offerings at your Goddesships’ shrine. But if, conformable to your usual discernment, you are content with being a mere mortal, and require no other incense, than is justly due to you, I will talk to you like one [in] his sober senses; and, though it may be straining the point a little, I will even stipulate to pay you all the rational tribute properly applicable to a fine girl.
But amidst my amorous transports, let me not forget, that I am also to perform the part of a politician and intelligencer. This however will not take up much time, as the present situation of things gives birth to very little worth notice, though it seems pregnant with something of importance. The enemy, from some late movements, appear to be brooding mischief, which must soon break out, but I hope it will turn to their own ruin. To speak plainly, there is reason to believe, they are upon the point of attempting some important entreprize. Philadelphia in the opinion of most people, is their object. I hope they may be disappointed.
Of this, I am pretty confident, that the ensuing campaign will effectually put to death all their hopes; and establish the success of our cause beyond a doubt. You and I, as well as our neighbours, are deeply interested to pray for victory, and its necessary attendant peace; as, among other good effects, they would remove those obstacles, which now lie in the way of that most delectable thing, called matrimony;—a state, which, with a kind of magnetic force, attracts every breast to it, in which sensibility has a place, in spite of the resistance it encounters in the dull admonitions of prudence, which is so prudish and perverse a dame, as to be at perpetual variance with it.
Hamilton Biographers Opine
Hamilton biographers have much to say about this letter.
James T. Flexner noted, “Unless we assume a previous heavy flirtation, which the entire context of Hamilton’s communication seems to exclude, the young man is trying to pounce on the older woman with the suddenness of a tiger.”
Ron Chernow delved even deeper into Hamilton’s psyche:
One thing grew crystal clear at Morristown: Hamilton was girl crazy and brimming with libido. Throughout his career, at unlikely moments, he tended to grow flirtatious, almost giddy, with women. No sooner had he joined Washington’s staff than he began to woo his old friend Catherine Livingston, daughter of his former patron, William Livingston, now the first governor of an independent New Jersey. In an April 11 letter to Kitty, Hamilton struck the note of badinage favored by young rakes of the day… That Hamilton was being more than playful with Kitty Livingston is shown in his declaration in the letter that the end of the Revolution would “remove those obstacles which now lie in the way of that most delectable thing called matrimony.”
Based on the above excerpt from Hamilton’s letter and the analyses of biographers, one could very well conclude that Hamilton, in his letter to Kitty Livingston, was on a romantic mission with courtship in mind. But a further analysis of the letter and a deeper understanding of its context cast doubts on this conclusion.
Hamilton Encouraged to Write to Kitty
The above excerpt, which is often quoted, was preceded by a more mundane paragraph, which biographers often neglect to quote or even mention. Hamilton opened his letter to Kitty with:
I take pleasure in transmitting you a letter, committed to my care, by your Sister Miss Suky, and in executing a promise, I gave her, of making an advance towards a correspondence with you. She says you discover, in all your letters to her, a relish for politics, which she thinks my situation qualifies me better for gratifying, than would be in her power; and from a desire to accommodate you in this particular, as well as to get rid of what she calls a difficult task to herself, and to give me an opportunity of enjoying the felicity which must naturally attend it, she wishes me to engage on the footing of a political correspondent.
Thus, Susanna “Suky” Livingston had written a letter to her sister and asked Hamilton, as an aide-de-camp to General Washington, to transmit it to her. Suky also encouraged Hamilton to write to Kitty. The purpose of Hamilton opening this correspondence, according to what Suky told him, was to discuss politics. But Hamilton must have assumed that Suky had more than just a political correspondence in mind. He must have thought that Suky was trying to initiate a correspondence between him and Kitty for the purpose of a courtship.
Even if Suky did not have this in mind, why wouldn’t a young bachelor make the most of the opportunity provided him? Yes, Hamilton was willing to be Kitty’s political correspondent, but he was also open to the idea that he could be something more, but he left that decision to Suky.
It will also be noticed that at this early stage of their potential courtship, Hamilton wrote nothing about his love or affection for Kitty. Hamilton struck a playful tone that touched upon the topics of love and marriage, asking Kitty what she thought about the possibility of going down that path, but without expressing any affection for her. He likened Kitty to a “goddess” if she chose to be one or “a fine girl” as he knew her to be, but he never actually expressed his emotions for her. Just compare the nature of this letter to those Hamilton wrote to Elizabeth Schuyler during their courtship and those to her family during that period, which contain much less bravado but infinitely more warmth and affection.
In this letter to Kitty, Hamilton was writing in a style meant to impress rather than one meant to convey one’s feelings. This flirtatious, over-the-top style was all the rage during this period. It often included allusions to love, sexual desires, matrimony, and intercourse. Among the most popular novels of this time was The Life and Opinions of Tristram Shandy, Gentleman by Laurence Sterne, which was known to be “the dirtiest novel in English.” The gentlemen and ladies of society participated whole heartedly in this good-natured fun. Martha Daingerfield Bland described how “General Washington,” a man known for his Stoic composure, “throws of[f] the Hero” whenever he joins a riding party “and takes on the chatty agreable companion—he can be down right impudent sometimes.” And the women loved it. “Such impudence,” Bland continued, “as you and I like.” Similarly, Angelica Church wrote to Elizabeth Hamilton in 1795 with the wish that Alexander “shall not talk politics to us. A little of his agreeable nonsense will do us more good.”
As men were expected, in appropriate situations, to write and speak in this style and women appreciated it and often reciprocated, Alexander Hamilton put his brilliant mind, quick wit, and able pen to the task of mastering this form of communication. Accordingly, Alexander Hamilton would later explain to Angelica Church, “I seldom write to a lady without fancying the relation of lover and mistress. It has a very inspiring effect.” And this was exactly how Hamilton had written to Kitty Livingston.
Hamilton Knew Kitty Livingston
It will be recalled that Alexander Hamilton had lived with William Livingston in Elizabethtown, New Jersey, back in 1772–73. During this time, Hamilton befriended Suky and Kitty, as they were both living with their father. Accordingly, Hamilton knew Kitty well and must have known that she enjoyed this style of banter. In fact, in his letter to Kitty, Hamilton had written of “my knowlege of you” and how he already knew about Kitty’s “usual discernment.”
Moreover, Hamilton must have expected that Kitty would tell Suky and perhaps her father, Governor William Livingston, about what Hamilton had written to her. Perhaps Kitty would even show them Hamilton’s letter. Knowing this, Hamilton would never have written anything inappropriate. Although the letter might seem overly forthcoming to our modern ears, this was the kind of writing that would not have embarrassed the author if it were to be shown to others. Accordingly, Hamilton’s letter should not be seen as a love letter. Rather, it was written as a work of literature designed to amuse and impress the recipient.
Some previous Hamilton biographers have noted correctly the context in which this letter was written. Mary Jo Kline wrote, “Alexander Hamilton’s courtship of ‘Kitty’ Livingston should not be taken seriously. Five years his senior [sic], Catharine enjoyed flirting and flattery.” James T. Flexner noted, “Susanna (Suky) encouraged Hamilton to write her sister Catherine… The general tone of this epistle is in keeping with the flirtatious idioms of the time. A parody of pretentious metaphors, it makes fun both of the writer and the recipient… As for the bantering generalizations concerning the opposite sex, they were an accepted convention, perhaps because they served as a nonphysical and impersonal way of keeping in the foreground that the communication was a sexual one. Both women and men teased each other with presumably witty allegations unflattering to their correspondent’s gender.” However, these biographers are in the minority, and in the case of Flexner, despite noting that this was the style of the era and that Suky initiated the conversation between Hamilton and Kitty, he still concluded, as noted above, that Hamilton was a “young man…trying to pounce on the older woman with the suddenness of a tiger.”
Thus, one who reads the Hamilton biographies by Ron Chernow, James T. Flexner, and most other writers is left with the impression that Alexander Hamilton was “girl crazy and brimming with libido” and that he pursued Kitty Livingston like a “young man…trying to pounce on the older woman with the suddenness of a tiger.”
But the reality is quite different. Alexander Hamilton was writing to an old friend in the style of the time. A mutual friend had encouraged Hamilton to write to Kitty Livingston, which he did, probably thinking that the purpose was to see if a romantic relationship could develop. Alexander Hamilton’s offer to go on “excursions in the flowery walks, and roseate bowers of Cupid” was not an attempt to “pounce” on Kitty Livingston. Rather, if Hamilton was not just writing in the style of the time and in fact was serious about pursuing a romantic relationship with Kitty, his letter should then be seen as an offer to become better acquainted with courtship in mind. This would be akin in today’s world to asking someone out on a first date. This could lead to something more, but it might not, and it is merely an expression of interest rather than love. Accordingly, Hamilton’s letter is full of the boastful, flirtatious language that was popular at the time, but made no mention of any affection for Kitty or a desire to marry her, for it was way too early in their relationship, which did not even exist yet, to express such feelings except in broad terms of the other gender.
Desiring to write the most sensational and tantalizing narratives, it is clear that many Hamilton biographers simply go too far when writing about Alexander Hamilton’s letter to Kitty Livingston. It is nothing more than a wonderful piece of literature, if one enjoys the flirtatious, over-the-top style of the day, as Hamilton knew Kitty would.
© Posted on May 7, 2018, by Michael E. Newton. Please cite this blog post when writing about these new discoveries.
 For instance, see Alexander Hamilton to Margarita Schuyler, February 1780, in The Papers of Alexander Hamilton 2:269–271; Alexander Hamilton to Elizabeth Schuyler, March 17, 1780, in ibid. 2:285–287.
 Martha Daingerfield Bland to Frances Bland Randolph, May 12, 1777, in Proceedings of the New Jersey Historical Society 51:152.
 Kline, Alexander Hamilton: A Biography in His Own Words 1:54.