In December of 1779, a twenty-four year-old Alexander Hamilton wrote to his friend John Laurens, asking Laurens to find for him a wife in South Carolina:

“She must be young, handsome (I lay most stress upon a good shape), sensible (a little learning will do), well bred, chaste and tender (I am an enthusiast in my notions of fidelity and fondness); of some good nature, a great deal of generosity (she must neither love money nor scolding, for I dislike equally a termagant and an economist). In politics, I am indifferent what side she may be of. I think I have arguments that will safely convert her to mine. As to religion a moderate stock will satisfy me: she must believe in God and hate a saint. But as to fortune, the larger stock of that the better…”

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From a December 1779 letter from Alexander Hamilton to John Laurens. You can find more of Hamilton’s words, from adolescence to adulthood, in the definitive Alexander Hamilton: Writings.

In December 14th of the following year, Hamilton married Elizabeth Schuyler of Albany. Schuyler, whose mother Catherine Van Rensselaer was from one of New York’s most powerful and privileged families, and whose father, Philip Schuyler, was a decorated general of the Revolutionary War, eventually bore eight children before Alexander was killed in a duel in 1804.

Elizabeth, or Betsy as she was known, survived a half century after her husband’s untimely death, during which time she dedicated herself to helping dispossessed widows and founded New York’s first private orphanage, the New York Orphan Asylum Society. She is pictured below.

P.S. In closing this same letter, Hamilton wrote:

You will be pleased to recollect in your negotiations that I have no invincible antipathy to the maidenly beauties, and that I am willing to take the trouble of them upon myself.

If you should not readily meet with a lady that you think answers my description, you can only advertise in the public papers, and doubtless you will hear of many competitors for most of the qualifications required, who will be glad to become candidates for such a prize as I am. To excite their emulations it will be necessary for you to give an account of the lover—his size, make, qualities of mind and body, achievements, expectations, fortune, etc. In drawing my picture you will no doubt be civil to your friend, mind you do justice to the length of my nose, and don’t forget that I——

After reviewing what I have written, I am ready to ask myself what could have put it into my head to hazard this jeu de folie. Do I want a wife? No. I have plagues enough without desiring to add to the number that greatest of all; and if I were silly enough to do it I should take care how I employed a proxy. Did I mean to show my wit? If I did, I am sure I have missed my aim. 

I believe I can pick up most of the innuendo in this. Maidenly is a euphemism for virgin, while size and nose are substitutes for… well, you get the point. And at that, one’s tempted to just shrug boys will be boys, and put away the Hamilton letter for another day; that is, until the recognition hits you that it’s the author of Federalist No. 84 who’s making the lurid emails sent amongst your college buds look tame.

Yet there’s something warmly reassuring to these words. They’re a reminder that history is both linear and cyclical, that lives pass but that the pressures and preoccupations (and in this case the puerile sex jokes) repeat in each generation. Shakespeare’s horn and lance gags and even the snake imagery of Michelangelo’s Sistine Chapel ceiling betray the fact even our greatest geniuses were thinking and laughing about the same stuff you and I do.

To read a condensed but daunting biography of Hamilton, and see how his story contrasts with that of his political rival Thomas Jefferson, click below:

Jefferson, Hamilton, and the Art of Power