Hurrah for senior Azurcrests! Henrietta gets along with most (if not all) of her housemates so she'll be friendly with Ryan. And if you want them to be ~extra friendly~ then I'm up for them being exes or random makeout buddies. She'll just be like "lol okay w/e" at his moods and shrug them off without getting offended.

As for Pippa, I don't think there's much overlap between them but Essie is showing Pippa all the cute boys at this school, so she may giggle and blush when she next sees him~