Do you think you are becoming his link to his past? Someone he needs to check in with on occasion for some sense of comfort. If you could take yourself out of the equation, and insert anyone else in the world into his chain of contact, who would it be?
A family member who is passed or out of contact? Someone from his past who he feels he has lost touch with? Or is it possible he does not feel that you two are lost ... but only unable to maintain the desired level of closeness for now?
He is a confused one ... and he is confusing to you.
So, do you answer him as if the vet had texted to say how is puppy? Or do you offer up some brief piece of puppy interest that he will feel he is missing out on? I don't think he is wanting to hear "puppy is ok".
I think he is wanting to hear some little story about what you and puppy did today, as if he were in another world and needed this news to stay connected to earth until his return.