This thread is fascinating.
Simply stating that something is forbidden doesn’t make it not so. This person clearly understands that she is meant to forgive while also being cognizant of the fact that she is having a hard time completing this mitzvah with her whole heart — which is the only way to do them, no?
So, she is left sitting on the horns of a dilemma.
Much of the information she has received here seems as though it would be helpful, and I hope I can add to that with my thoughts.
1. I like that Kollel_Wife is so clear that this person is not deranged or unstable, just a normal person with a lack of sensitivity (or concern) about how his words/actions make others feel. This explanation shows you to be thoughtful and sensitive, and not trying to make this guy out to be just a jerk.
2. If you have not had any success trying to explain to this colleague that his way of communicating is not working for you, is there someone over his head to whom you can talk? I am not saying you should commit loshon hora, or try to get him in trouble, but most companies have some sort of policy designed to help those without social graces to get along with their colleagues and perhaps a reminder from someone more powerful than yourself would help this person get the message.
2a. If you are feeling this way, it is likely that you are not the only one. I bet that if you talk to a superior you will learn that you are not the first to complain — you might be the straw that breaks the bosses back, just what is needed to get this person the help he needs.
2b. Again, without gossiping, you might be able to find out if others feel as you do. There is power in numbers. If you all agree to speak with the boss independently over a few days, it will become clear that something needs to be done and most bosses will take the needs of the many for a pleasant workplace to heart.
3. If this guy IS the boss, that does make it trickier. But I didn’t get the impression that was the case here.
4. Labor law in most places states that if a work environment becomes toxic or unhealthy it is the responsibility of management to fix it, and you cannot be punished for filing a toxic work environment claim with the department of labor. This is a last-ditch response of course, however, if all of the above fail to get management to talk to the person in question, and/or if he fails to comply with their requests and they don’t get rid of him, it is something that is worth mentioning… maybe.
Everyone deserves to come to work in an environment that is at the least collegial and conducive to accomplishing the tasks at hand, and I hope that you are able to make that happen in your workplace. Something tells me that you are not the only one wishing for this individual to change his ways.
As far as what you are and are not obligated to do, it seems to me that you are working to the best of your ability to be truly forgiving. If my memory serves, we are absolved from those promises and/or obligations which we have made honest effort to accomplish but have been genuinely unable to do. This seems like one of those situations so, IMHO, you can go to services this Yom Kippur with a clear conscience in this regard.
Best of luck, and please let us know how it turns out…