1 thanks 
2 he's not asked this exact question, the "big eyes" thing is new, but he's asked variants of "If there was a person in real life that looked different, would you still treat them like a human/want to date them?". A lot of them have also been oddly gendered? Like one was "could you still find a female with blue skin attractive enough to date?" (female being his vernacular).
I don't think I've ever seen him ask a question about people would react to relationship situations or personality (unless you count "like Samson, is it foolish to put your trust in women because they will betray you?"), most of the time this hypothetical person's attitude isn't even mentionned, so over time there's really been a build up of the feeling that the underlying belief this kid has is that appearance is way more important in relationships than it actually is. Despite these threads always coming down to most people saying "that's odd but it depends on how they act" every time, the questions keep popping up with a different "weird" usually "alien" element we'd potentially judge a step too far.
From what I can tell, the kid's grown up in one of the more cult-ish sects of protestantism (not sure if it's JW, Mormonism, one of the new baptist ones or fundieland, but it's definitely one of them), and he's got very narrow views of what's normal, believes a lot of Bible stories are litteraly true (beyond the historical stuff like "yeah, there was a dude with that name who lived there around that time") and he's also definitely stumbling across some Bible-based conspiracy theories online too, like he's talked about some of the wilder stuff the flat earth guys used to say about aliens and fallen angels (nephilim have popped up). Sometimes he seems to be trying to reconcile the cognitive dissonance between what he's being told about the world, and how people in wider society react.