Olive was watching her son play in the yard.
Does she always watch him?
She obsessively watches him with a smile on her face
Well it is good to watch your children play. They could get hurt and it is good to make sure to respond fast when they do.
The smile on her face is some rabbit hole shit
That is not a good way to describe someone smiling. Everybody smiles in their own way. And while you don't have to think it is attractive, it doesn't mean that you should be mean about it. She must be happy to see  her son playing and talking badly about her might make her feel bad and sad.