@Red225 : Essentially, he'd like to see her let loose instead of upholding her 'perfect girl' image that she normally do in public.
So things like saying what she truly want, being a little selfish with her desire, all that sort of thing.
Given it's the prince, I'm guessing his desire would cap out at the floof level of lewd i.e. handholding, rather than 18+ intimacy (that will likely be brought by her after the marriage)
The girl herself is also stubborn, she want to know what it is that he got enamored with this time so she can study and pleases him just like all the previous times, but in maintaining her image she couldn't go and ask him to clarify it until he come to her crying.