What is hurtful speech?

[1] Do not say to a fellowman, “For how much would you sell this item?” when one has no desire to buy it. [Or,] if one seeks to buy grain, one should not tell him, “go to so-and-so,” when he knows that [the person he named] does not have any grain to sell.

[2] If his fellowman is a ba’al teshuvah [someone who repented], one should not say to him, “Remember your earlier deeds.” If a person was afflicted with suffering, may the All-Merciful forbid, one should not speak to him in a manner similar to the way Iyov’s friends spoke to Iyov:  (Iyov 4:6-7): “Can you not rely on your fear/awe of G-d”… Try to recall, please, did an innocent man ever perish?” They addressed him that way only because he had complained against Hashem’s Providence and His [actions’] attributes.

[3] If a person asks of him about some kind of art/wisdom, one should ask of someone who doesn’t know that art/wisdom, “What is your opinion of the matter?” The same applies with regard to similar matters which cause heart-ache.

The halakhah spells out three subtypes of ona’s devarim, and I turned the translation into a numbered list to make the point more evident.

1- Most similar to ona’as mamon, hurtful business practices, is getting someone’s hopes up about a deal that you know is fictitious.

2- Outright insult.

3- Saying something that one knows will embarass someone or cause them other emotional pain. This would seem to me to be more insidious than the previous category, since it includes an element of mirmah, duplicity. The victim could never know that the speaker intended harm, and could continue to trust him,