Is this annoying for managers? No doubt. But, well, that’s why they’re paid more than you. Like a lot of bad managers, yours wants to have it both ways: to get paid more money without extra responsibility, and to be your buddy while still wielding power over you. He wants to use your ambiguous but pleasant interpersonal relationship to set the terms of what is, in fact, a clear professional relationship. This is exactly backward. A real friendship in the workplace can be cultivated only in the context of a settled professional relationship.