> I think a convincing example is to show a heads-up display of what two people last talked about as to enrich the conversation.

Perhaps. It might be a generation or two before the "that's ... creepy" vibes fade. Reminds me a bit of that scene in minority report after the eye swap and the protagonist passes by a billboard and the avatar asks him about how the pants he purchased worked out.

I do something similar to the calendar thing too. I reach out a few days ahead of time so it doesn't seem like I'm just doing it reflexively like an unfeeling robot because facebook prompted me to do so day of.