In my case, I don't think the DMV lady was trying to 'care'. I'm going from a feminine name to a masculine name; I'm early in transition and I do not pass yet. If she'd only said it once I would have rolled my eyes and moved on, but she kept picking on the matter, like she was trying to needle me for giving up a pretty and feminine name.
All the other people I've dealt with during this name change (and this has been around a dozen) have been polite and pleasant, with some commenting on my interesting and nice new name. Those were the ones who showed some caring and I did appreciate them quite a bit.