very interesting, I have learned a few things while reading this.
First(1), I will post some of my experiences and then(2) some thoughts about and some thoughts about how to gain a better ability in "empathy-related-thingies".
(1)
I find the funeral example (with the boss) really interesting, because I really relate "bad" to funerals or funeral scenes in movies, I always thought it was due to my past (high mortality rate in my family), but it seems not to be only that. But as mentioned by a member before past experiences are the key. (see (2))
I personally think empathy or to empathize etc. can be learned, WHY?
(a) Experience:
I found this "list" on the net:
http://web.archive.org/web/2003080307413...ndrome.htm
There are a lot of points I have, but also a lot I had and I managed, for instance: Maintaining eye contact with persons of the same sex it was no problem since a few years, and in the last year I even managed it to the point that person of the other sex can keep up.
(b) Research:
you know "leaders are born, not made" -> bullshit
you know "charismatic people are born and you can't learn it" -> bull ***
you know "experts are born, not made" -> bullshit (see Expert Mind - Scientific American)
most things are just "comforting limiting beliefs", nothing more and nothing less.
(2)
I listened to the audiobook form Goleman about Emotional Intelligence and I am also reading now: Primal Leadership (which is EI + Leadership + how to make it).
The one thing which strikes me now with the information of the books, my experience and this posts combined is this:
Self-Awareness is the base for the being empathic.
Why?
1) It is written in the book.

2) Past experiences:
a) I can relate to funerals, BUT
b) I can't empathize to a friend who gets a present he really enjoys and I see it, but I can't fell anything, WHY? I didn't knew, but now I can't imagine a present that I will get, which would make me really happy. So I simply don't know/have this feeling.
I also realized, that I sometimes don't know in which "state" I am in, also friends reported you are just top or down. Well that's an aspie trait, but maybe we just need to listen/monitor a little bit better. (In EI Goleman writes about that they do it with children, they monitor their own feelings, but I lack a guide for doing this. I guess it is connecting the rationale and emotional parts of ourselves.)
Aspies are know for having only extreme emotions, to some part I guess, we shutdown some of them for selfdefense. It is just a habit, like other social skills, they are "hard wired" (but not fixed) in some parts of the brain. (Goleman explains that some things (rational) you hear once and get em, but "habits"-thingies are only relearned due to practice and actively doing them.)
So this would mean, it is necessary to develop emotions/feelings for "normal day life" or recognizing the active state and doing it so often, that it gets "automatic. Maybe even imaging feelings, but such ones that are "unknown".
Another point:
Body language, since Aspies lack "body language skills" it is useful to use it more actively, because the body and mind interacts all the way, the question is not what goes first, but what helps me doing the thing I want to, because bringning yourself in a body language position that is usually use in decision-making also triggers in some parts a decision-making process in your brain. (I am not quite sure about this, but I think there was a story about a family where the learnt empathy for each other due to mimicking the other persons body language, tone etc. but in more extreme way to actually feel it.)