At this point, there s no need to involve upper management. It s not really making everyone uncomfortable, just you, and you should always try to resolve a situation like this directly before you go over anyone s head. Why not just tell your boss the next time he starts divulging information that the information makes you uncomfortable, and you would prefer he not share it with you. Or just don t go out drinking with him.He is not breaking any privacy laws currently in existence. What happens in the workplace is not necessarily private. As you are both employees in the same company, and the same department, there is no breech of any law. But go to upper management, as you seem to have your mind made up. Good luck.
i disagree with the other yahoo answerer; go tell management what occurs during theseoutings.I think they will not be happy. Also volunteer that you would like to climb in management.