Haha I knew this would come up. 
Indeed.
If that were what I’m optimizing for (emotional comfort), then indeed, you’d be right.
I think it was (helpful), for it made the situation clearer. For Leila’s own benefit. She might not have seen it at the time, and you might not have either. I’m still confident it had to be done.
My purpose here is, to the extent that I can, to help people achieve actual freedom. This takes many forms as people (identities) come in many forms, and find themselves hold up at many stages, with many obstacles.
You might have noticed I’m pretty laid back usually, not intervening much, content to watch people figuring stuff out for themselves. I sometimes intervene when it appears that a nudge, a hint, an allusion, might be enough to help people see something, or go over some hurdle. They’re free to do whatever they want with it, it’s not like it’s my responsibility what people do with their lives. And I certainly don’t picture myself a guru, a teacher, a guide or whatever.
When I see someone stuck in a particular problematic situation (as regards one’s progress towards actual freedom), not showing sufficient or impending clarity about it that would let one think that they’re about to go over it, my intervention (if it happens) may be less subtle. It may be as plain as it needs to be.
Actually this has changed somewhat, for I would indeed have let these states of affairs slide, one or two years ago. And I did. Allowing people to linger in the comfort of their ignorance about their own stuff. Allowing them to turn around on themselves for years, blocked in their progress. Which I saw as respecting people’s freedom, but now see as kinda giving-up on people. So you might say that my (actual) caring has increased… even if it might look like the opposite from a feeling-caring point of view 
.