In February 1780, Hamilton wrote a letter to Eliza’s younger sister, Margarita (nicknamed Peggy) to introduce himself. At this time, he hadn’t met Peggy, but he had heard about her from Eliza.
I venture to tell you in confidence, that by some odd contrivance or other, your sister has found out the secret of interesting me in every thing that concerns her; and though I have not the happiness of a personal acquaintance with you, I have had the good fortune to see several very pretty pictures of your person and mind which have inspired me with a more than common partiality for both.
You will no doubt admit it as a full proof of my frankness and good opinion of you, that I with so little ceremony introduce myself to your acquaintance and at the first step make you my confident.
Hamilton playfully described having “serious and henious” charges to make against Eliza because of her beauty and charm:
I have some things of a very serious and heinous nature to lay to her charge. She is most unmercifully handsome and so perverse that she has none of those pretty affectations which are the prerogatives of beauty.
Hamilton’s description is framed in the difference between Eliza and all other women in society, who Hamilton characterized as being frivolous and foolish. His backhanded compliments wouldn’t be out of place in a modern day dating website.
Her good sense is destitute of that happy mixture of vanity and ostentation which would make it conspicuous to the whole tribe of fools and foplings as well as to men of understanding so that as the matter now stands it is ⟨very⟩ little known beyond the circle of these. She has good nature affability and vivacity unembellished with that charming frivolousiness which is justly deemed one of the principal accomplishments of a belle. In short she is so strange a creature that she possesses all the beauties virtues and graces of her sex without any of those amiable defects, which from their general prevalence are esteemed by connoisseurs necessary shades in the character of a fine woman.
Hamilton joked that Eliza was breaking hearts and turning heads all over Morristown.
I should never have done, were I to attempt to give you a catalogue of the whole, of all the hearts she has vanquished, of all the heads she has turned, of all the philosophers she has unmade, or of all the inconstants she has fixed to the great prejudice of the general service of the female world.
He told Peggy that Eliza’s influence was so strong, that to preserve the safety of the state and the army she needed to be removed from the neighborhood:
It is essential to the safety of the state and to the tranquillity of the army that one of two things take place; either that she be immediately removed from our neighbourhood, or that some other nymph qualified to maintain an equal sway come into it. By dividing her empire it will be weakened and she will be much less dangerous when she has a rival equal in charms to dispute the prize with her.