It's cute that they're finally close/comfortable with each other enough to have this kind of conversation at this point. I feel like even where we are now in the main chapters (which at minimum is about a week before this could take place) his insecurity would be screaming "DON'T TALK ABOUT SHIT LIKE THAT SHE'LL THINK IT'S CREEPY NEVERMIND THE FACT THAT SHE'S THE ONE WHO TOOK THE CONVERSATION HERE IN THE FIRST PLACE SHE'LL STILL THINK IT'S CREEPY BECAUSE I SAID SO" and give safe, boring answers rather than actually engaging in the conversation.