And when I do manage to get it sincere, it sounds "creepy" since that's what "doing social conventions wrong" sounds like.

Oh! I think that's where a lot of my confusion comes from. I read "creepy" as not-trying-to-comply with social convention (aka entitled), while you meant it as trying-but-failing to comply.

I can totally see how one could read the post we are discussing as trying-but-failing. In person, it would be quite a bit awkward. But the interpretive conventions are a little different for an online comment - and it read as supportive on the conventions I apply to interpret online comments.