This is so hard because you know this isn’t the first time they’ve had this conversation. They probably have it every time he visits her. He squares his shoulders before he goes in there, and hopes for the best, relatively speaking. You can see it in his face in that second gif - the way he literally crumples when he sees that he’s lost her again.
So I finally cracked open my Princess Diaries special edition dvd, and immediately went to the bloopers, as you do, and decided that the internet needed even more reasons to love Julie Andrews. You’re welcome.