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."

Allow him to be in contact with whom?? confused

Puppy