#Thank God they didn't actually engage in the incest until James's daughter married her distant cousin

[yr-obedt-cicero]

I think you've made jokes about the family trying to marry Philip off, were you being serious or was it just a joke? ^^'

Half serious, and half exaggeration. It wasn't actually that consistent of a thing, but it is reappearing in family letters. With all the eggs being put into Philip's basket, you can really imagine Hamilton wasn't the only one who planned out Philip's life and had expectations for him. Once again, these cases aren't that serious, and Philip was rather young when he died so I don't think marriage was the family's highest priority—but I'm certain there was some pressure to find a good woman, especially since how traditions were back then was that the eldest's partner would help run the house and family when parents grew a bit old (Not exactly arranged marriages but something similar).

Anyway, the earliest mention of it is sometime in the March of 1782, when Philip was three/two months old. Hamilton writes to his close friend and fellow aide-de-camp, Richard Kidder Meade, that Eliza was so close with Meade's second wife, Mary Fitzhugh Grymes Randolph, that they should have their kids marry so they could become in-laws;

Imagine my Dear Friend what pleasure it must give Eliza & myself to know that Mrs. Meade interests herself in us, without a personal acquaintance we have been long attached to her. My visit at Mr. Fitzhughs confirmed my partiality. Betsy is so fond of your family that she proposes to form a match between her Boy & your girl provided you will engage to make the latter as amiable as her mother.

Source — Alexander Hamilton to Richard Kidder Meade, [March 1782]

A more common occurrence was Angelica Church and her eagerness to have her daughters married off. She writes to Eliza and tells her to remind Philip - who was twelve during this time - of his “pretty cousin”, Elizabeth Matilda Church—she was only a year younger than Philip;

Adieu my dear Eliza. Embrace all the children and tell Philip that he is not to forget his cousin Eliza, she is very pretty and very good.

Source — Angelica Church to Elizabeth Hamilton, [January 25, 1794]

Again, just nearly a year later, she mentions a son of Eliza's should have Eliza M. or Angelica Church Jr as a wife. It isn't specified which son she is referring to, but it is likely Philip who seems to have regularly corresponded with his cousins on the Church's side of the family, and was relatively close with some members like Philip Church. Additionally, she describes the son as being a “chip off the old block”, meaning someone who is very similar in character to their father or mother, a coined characteristic Angelica had previously given Philip several times before;

My children are acting a play, they have a small theater in the drawing room and there performance is not very bad. Your son they tell me for wit and abilities is a child of the old Block. He shall have Eliza Angelica, for a wife.

Source — Angelica Church to Elizabeth Hamilton, [February 4, 1795]

But there was that time she wanted to have Alexander Jr and Eliza M. suited just five years prior, so this last one is a bit more of a dubious case. [x]