I used to have thoughts like this too. Like "Chris can't be THAT delusional/stupid can he?" etc. I've come to realize after following his antics for 6 or 7 years is that yes he can be that dumb and delusional but maybe not in the way normal people would think. Like for example, I think
@Marvin said it best about his delusions about attractiveness in the colorblindness analogy.
I think it also has to do with the fact that Chris has very fuzzy nebulous 'feelings' rather than straight line logic on a lot of things. Like people turn on their computers and assume if its plugged in and the display is connected it will work. They don't think about how a zillion electrons pass over tiny pathways a billion times a second to create images and virtual landscapes etc...in fact its kind of mind boggling when you really get down to it. That's how it seems to me that Chris sees a lot of basic interactions in life.
Like say Chris thinks he has a cute outfit. In the back of his mind is the 'I feel pretty' feeling and the vague idea that girls like cute outfits, he would compliment someone on their cute outfit so he wouldn't get why its terrifying to others on a beer-gutted, chicken legged, stubbly man. Trying to think about why people have issues with his look and behavior for him is like someone pondering the point of the universe to most people, its a deep thought and there may ultimately be no real clear answer.