What is the proper way for a child to handle a situation in which a parent says things to him/her that are hurtful — like asking, “Why is so-and-so popular and you’re not?”
I would think that it is wrong, not only to just say things like that to one’s child, but also to put the child in a situation where he or she is likely to be disrespectful (i.e. “talk back”) in self-defense. I don’t see Judaism teaching parents to make their children feel badly. Also, how does self-esteem fit in here?
It is, of course, prohibited by Torah law to cause any psychological hurt or damage to any human being – even one’s own child. The Talmud similarly prohibits a parent from placing his child in a position where he might be unable (or unlikely) to refrain from striking back in revenge. And while a Jew must be constantly self-critical of his own weaknesses, there must be an inner sense of his own self-worth underlying it all, or he will be unable to continue the struggle. Nevertheless, there are actually times when rebuke (which is, by definition, unpleasant) is not only permitted, but required (see Leviticus 19:17).
To be able to assess a situation, and know when a particular act of rebuke is both appropriate and measured, requires great wisdom and isn’t really possible from a distance. I suppose it would be obvious to remark that there are often times when very painful encounters can lead to greater progress and development. Yet, there are also many, many times when rebuke can be the product of insensitivity and can be both fruitless and scarring.
I hope this is of some help, and wish you the very best!
Rabbi Boruch Clinton