This i have mixed feelings on. Thomgelica.

Jefferson was friends with Angelica, but also she scared him off by slapping him. This could possibly make Jefferson more submissive in said ship. Historically Jefferson wanted "intelligent, talented, a good companion, and, a good homemaker" which Angelica would most likely be able to fill, with a little work on the last category. Jefferson was also a romantic who tried to emotionally connect before intimacy which when combined with some of his beliefs makes him a little ahead of his time just like Angelica. These two would not be a bad match.

Pros:
They were friends irl
Both ahead of their time
Angelica matches Jefferson's ideal

Cons:
Angelica isn't exactly smitten with him
It isn't as good as Jeffmads

My rating: 5/10