If you take that Machiavellian idea one step further... How about shifting the view of who to take advice from. People can only make you more like themselves... so only take advice, in any particular area, from someone who has ALREADY ACHIEVED the results you are seeking... otherwise, what is the point?

Also, though, your boss should not 'become offended' if you treated them as a drinking buddy... that would be unprofessional on HIS part... he should have a discussion with you, in a rational manner, about the roles that you both are to play in your working environment. I do not agree that people have certain areas where they would 'benefit' from being offended. Being offended often simply validates the person being offended, not matter what the offended person retorts with. If someone is rude to you in some way, and then you are rude back, it just makes the first rude person feel justified in their being rude to you in the first place.

If someone is INTENDING to be insulting to you, then rising to the occasion only proves to them that they have power over you. If they were NOT intending to be insulting to you, then all you have done is proven how much of a boob you are.