So...Alexander and Angelica. Let's do this. So in fandom it's kind of canon because they were close but probably not romantically involved. In fandom Angelica has a crush on Alexander but I mean who doesn't? A LOT of people had crushes on Alexander. I am not hating on Hamilton but I think the letter part of take a break kind of makes it seem like they want to be together romantically and makes Alexander look more disloyal than he actually was.
In real life their letters were flirtatious but that's just Alexander's natural state.
When Angelica met Alexander she already was married and had two kids. She eloped with John Church. She most likely wouldn't do that unless she loved him. So the line "I languished in a loveless marriage in London I lived only to read your letters" isn't necessarily true.
Now about the letters Angelica once wrote to Eliza, "If you were as generous as the old Romans, you would lend him to me for a little while." Also in fandom, Angelica spirals after Alexander writes, "My dearest, Angelica," suggesting she was his beloved. But it was actually Alexander who did that with Angelica's punctuation in a letter dated to 1787. Angelica wrote "Indeed my dear, Sir". Alexander said, "There was a most critical comma in your last letter. It is my interest that it should have been designed; but I presume it was accidental. Unriddle this if you can. The proof that you do it rightly may be given by the omission or repetition of the same mistake in your next,"
There is no proof that their flirtatious letters ever led to an affair. In Ron Chernow's biography on Alexander Hamilton he says, "It seems plausible that Hamilton would have proposed to Angelica, not to Eliza, if the older sister had been eligible. Angelica was more Hamilton's counterpart than Eliza." This actually would make sense. If there was love going on it was probably one sided. Based on these letters it seems like Hamilton was not as interested in her as she was with him. Another reason that this relationship probably would never have happened is because they both were too loyal to Eliza to do that.
But in fandom I would probably ship Hamgelica if Eliza didn't love him and wasn't married to him. And since Angelica was already married it would probably be very similar to Burrdosia at that point. American soldier who falls in love with a woman who is married to an Englishman. But of course Eliza exists and Eliza lives Alexander and Alexander loves Eliza.
This ship probably wasn't real because again they wouldn't do that to Eliza. Even though many people thought that they were lovers. Overall this is a very interesting ship that is really fun to explore and research but not true.
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Hamilton Ships
FanfictionThis is a book discussing all of the Hamilton ships and there probability both in history and in fandom. And also explaining them.