This is what peeling back a single layer is. I can only understand and sympathize with the GP's position to some extent, a lot of these "check yourself" replies seem very well put, but it's absolutely the case that there are people who for lack of a better term can be called unthinking. A more insulting turn of phrase might be "NPC". "Why did you find yourself interested in wine?" Not unrealistic answer: "Haha I dunno I just like the flavors, was introduced to it by x." Circle around to the topic again, they'll repeat that, and might not even remember you already talked about it. Trying to decompose "flavors" with them (whether you care or not) is unlikely to bear fruit.
Talking about their relationship with X is a logical follow on, of course, and has more fruit-bearing potential. I think one can have interesting conversations with everyone and it's important to converse with a variety of humans (fellow office workers of any profession being a tiny sample) but sometimes you can only hope to go for breadth, not so much depth. It takes the patience and training of a clinical psychologist to get anywhere with some people, and it's not often worth it.
Talking about their relationship with X is a logical follow on, of course, and has more fruit-bearing potential. I think one can have interesting conversations with everyone and it's important to converse with a variety of humans (fellow office workers of any profession being a tiny sample) but sometimes you can only hope to go for breadth, not so much depth. It takes the patience and training of a clinical psychologist to get anywhere with some people, and it's not often worth it.