You know, I'm a fairly sarcastic person, so had you said something like that to me, I would have thought you were being sarcastic, or funny. I'm sorry he had a bad reaction, but I would take it in the fashion it was given (at least it seems like what you are saying), and just accept it was a kidding kind of thing that he just didn't "get".

Don't be so hard on yourself.

And you are a fantastic writer. You paint a beautiful picture with your words.