I don't recall exactly what the triggering event was, but there was some minor event that went wrong for Leonarda at work the other day. As is my nature, I responded by scoffing at her bad luck. Then I stopped, looked directly at her, and said, "I'm sorry that isn't working for you."
Her head whipped around from the computer and she stared at me. "What was that?" she asked.
"I'm working on my empathy!" I exclaimed proudly.
"Wow. That is not working for you." she said, shivering slightly.
In fact, I was not working on my empathy. Although I've had numerous discussions with my wife over the years about the appropriate way to respond to people under duress, we hadn't had such a discussion in a couple months, so it's like those conversations never happened. (And, yes, I am aware that I was poorly imitating sympathy and not empathy). That being said, it never hurts to bone up on your humanity.
I've played this game multiple times at work now and gotten similarly horrified reactions. When Leonarda had a cold and I offered, "You must feel terrible with that cold. Having a cold is no fun." I got the following reactions from my co-workers:
"That is really disturbing, Mike."
"You're smirking while you say it! No smirking!"
"Wow, that's creepy."
"Maybe, if I didn't know you, I'd think that was genuine, but you can't pull it off. No way."
"It's the underlying layer of snark that gives you away."
Apparently I am the Uncanny Valley of empathy.