Should I be offended if my boss almost never looks me in the eye?
One or more of the following may be the reason:
The boss is introverted and does not like socializing. When she/he is talking to her/his subordinate, the purpose is to discuss official work, give instructions and be done.
The boss believes in a boss-subordinate hierarchy: The subordinate has to be fully attentive while the boss speaks. The boss can do ten other things while speaking to the subordinate.
The boss is insecure. She/he does not like being questioned or contradicted. She/he can deal with the situation better if she/he is not looking at you when such a situation arises. The boss does not want her/his face to express what she/he is feeling. The boss’s feeling of insecurity may also be because she/he feels that you are smarter.
The boss is a busy person and she/he wants you to know it. Smiling, laughing, facial expressions and extraneous topics are time-wasters for her/him.
You are good looking :-) The boss skips a heartbeat when you enter her/his room.
So, whatever be the case. The reason lies in the boss. It is better to have a boss who looks at your shoulder or stares at the wall while talking to you rather than a boss who has a glad eye and finds enjoyment looking at the wrong places.