What if... Emma has a brother, or something, who is either a squire or a page in the Order, and for whatever reason, Emma can't actually be Emma when she inquires after him. We can say that it's a rule: no family, no fraternization outside of the Order. As such, Emma dons the apparel of the old woman, and she cozies up that way to Kale. This goes on for a couple of years, until the brother dies in battle. A distraught Prince would then recount to the old woman how the "lad fought so bravely," never knowing that he was telling Emma the horrible news.
Perhaps then Emma would race home, as Kale is personally going to deliver the news to her parents in the city, and she intercepts him there. Maybe that could be their one and only meeting.