The empathy instinct - anyone without successfully develop it?

JerseyFrank went on a bit of a rant said
8

First, a definition so that we're all on the same page:

em·pa·thy: the ability to understand and share the feelings of another.

I can empathize with people; that is, I can put myself in their shoes - but it's never instinctual. This causes me more grief than I'd like. I often hear someone's happy news and when there's an obvious (to me) down side that no one is commenting on, I don't pile on the happy train. My instinct is to go straight to bottom and be the wet blanket.

Case in point: An old friend's daughter just scheduled her first college visit to the University of Miami. Everyone was all, "Wow!" "Congrats!" "Your daughter has grown so much!" "You should be proud!"

In hindsight, that's the correct response. I did not choose that. Instead, I told them that I went there and I wouldn't recommend it (to someone from my working-class hometown.) There are issues with financial aid (probably not unique to UM). But more importantly, it's a rich kid's school. You can't keep up socially when you aren't spending Mom & Dad's money.

That makes me an asshole. I don't mind being an asshole, but I don't want that to be the cause. I want to be an asshole on my own terms.

Have any of you suffered from the same social ineptitude? Have you done anything to fix it? Has it worked?