For starters, I would NOT allow him to talk about OW so casually to you. That is like the ULTIMATE personal boundary, and you need to nip that one right there: "I would ask that you don't talk about your girlfriend to me -- it's incredibly disrespectful, and I won't tolerate it."
What do you mean, "Now how do I handle next week? My instinct says to allow him to be in contact as she isn't around all week, but instincts never seem to be right with DBing."