Gradualism was something used by the missionaries to the Indians in what is now the US, but it was gradualism in the sense that they had to do certain basic things (give up polygamy, for example) if they wished to be baptized and then would live as catechumens for some time until it was decided that they understood the reasons for this, knew enough and were conformed enough to Christian moral teachings.
But there was always a goal, and the goal was not for the Church to accept the practice of the converts (such as polygamy) but for the converts to conform themselves to Christian morality and practice. In the meantime, they weren’t a full part of the community.
I think Monsignor makes a brilliant point about the difference between the pulpit and the confessional. I think outsiders may very well miss this very important point. Having had the pleasure of knowing some fine priests fairly well, I can attest to the need to strike a balance when homilizing. The last thing they want to do is make an individual think that everyone is looking at them. Far better to take this up in private and then the guidance can be individualized.
I have occasionally shared various pieces of advice given to me by priests in the past. I have had people say that it was not very nice of the priest to say that. Well I assure them that the priest said it because,
A: They knew me and what the issue was. B: It was fatherly advice. C: Priests are not POD people. They are sons, brothers, grandsons, friends, brothers in law etc. They do know a lot about human relationships. E: When they are in the confessional they are in Persona Christi, so of course they are the human whom Jesus speaks to you, through. F: They are very educated individuals who have a wide variety of interests and hobbies. They don't sit around all day contemplating their navels.
So in conclusion, just because a priest poses a question or scenario in a discussion, that does not mean that it is cast in stone.