Alice met Grayson when he was twenty-eight. He had quite a few misdeeds by this point. In the present day I write most of my fics in Alice is thirty-eight and Grayson is forty-eight. By that point, I would say Alice only knows about ten percent of his past misdeeds. She knows he was involved in a fight in high school that nearly got him expelled but very little else about the incident. She knows that his fiancée died after a car crash where he was the driver and that he feels responsible for her death but very little else.

Grayson is an intensely private individual. From my fic Pantomime Matrimony, "This man who took nearly five years of knowing her to tell her what town in France he spent every summer in until he turned twenty-five." Grayson doesn't share very deeply of himself and works even harder to hide previous wrongdoing, so Alice really is not in the know.