Oftentimes, some teachings of the Catholic Church seem, well, cruel. For instance, I read in the forum that a woman whose husband left HER cannot re-marry or even date. I understand that, but isn’t that a bit mean? Are any of the apologists ever uncomfortable with the answers they have to give? Do they ever attempt to say, “Gee, this might be blunt and hurtful… Maybe I need to phrase this differently?”
First, let’s make sure we distinguish between the Church’s teachings and the apologists’ answers. While the apologists make every effort to formulate answers that accurately reflect the teachings of the Catholic Church, the apologist answers should not be mistaken for the “teachings of the Catholic Church.” Your question really should be, “Are the apologists being cruel in how they respond to questions about Church teaching?”
We certainly try not to be cruel and cruelty is never our intent. I can only speak for myself, but I try to soften my wording whenever possible and to offer reasonable alternatives, explanation of logic, and promise of prayers. I am only blunt, shall we say, when I sense that someone needs bluntness rather than gentleness.
As for your particular example, I do not know which Q&A you are referring to, but if the woman in question was asking if she could date after her husband left her, the answer to such a question ordinarily is “no” and both honesty and the need the woman has for necessary information to rightly order her personal life demand that she be given that answer.