it's really hard to talk to someone who won't listen. lots of people guess what they think you mean, but didn't say, instead of listening. this is especially bad when there's culture clash. then they're making guesses given a different perspective than yours. that's not well suited for understanding your point.
it's hard enough to figure out what someone is purposely and directly trying to say. intentional, explicit communication often goes wrong. communication is hard. it involves guesses at their meaning and criticism to reduce errors. it requires thinking, learning.
reading between the lines is much harder than regular communication. people can't do this stuff, but try to do it all the time anyway, and fuck it up. the reason they think they can do it well is they've had some success with something else.
there is a way to get similar results to reading between the lines, without listening in a more literal way. it doesn't always work. but it does sometimes work. people don't realize what's going on, why it works, when it doesn't work.
what they do is assume the speaker or writer is conventional and the communication is stereotyped. this works when dealing with people who are stereotypical, rather than unique. (if you find it works with your friends, that's a sign that you and them are conventional, stereotypical people.)
rather than figuring out what ideas a statement could mean from the set of all ideas, people guess the meaning from only a small set of culturally common ideas. the meanings considered are further limited to a subculture and to the kind of situation or topic they think they're dealing with.
like, if they think you're discussing food, they will try to interpret what you say as having a conclusion about food. even if you are actually using food as an example to make a different point. like you could use stuff about learning to cook to make a point about learning. or you could use following a recipe to make a point about following instructions. or you could go from talking about food to talking about pressure for girls to be skinny, and fad diets. or you could talk about something unrelated and use a food thing as an example.
people often miss topic changes, although sometimes they notice. the more your topic is unconventional, the less they'll notice the change. in general if you say, "i am talking about Y, which is related to X", people often miss the transition if you aren't making a common argument they've heard before. then they don't really follow what you say about Y.
this is how most communication works: people try to figure out which idea they already know that the speaker or writer may mean. if you say something someone doesn't already know, they can't understand you.
because people are conformists who are used to interacting with other conformists, this approach to "communication" often seems to work for them. especially because it's polite to gloss over a 75% rate of misunderstandings. (by conformist i don't mean someone who says "conformity is good". i mean someone who acts like it. often they pretend to be unique rebels.)
so people think they actually have the skill of communicating. they think they're good at communication. but they aren't. then they try philosophy discussions or reading and have lots of misunderstandings. they don't know how to communicate well in general. they just know how to communicate a list of culturally standard things.
actually, to be more precise, it's like the more culturally normal an idea is, the easier they find it to communicate successfully about. it's a matter of degrees.
so people have a harder time learning ideas that are unusual to them. they aren't good at thinking outside their current perspectives. but they often don't take the blame for this. they will blame a philosophy like Objectivism for their own fault. they'll claim Objectivism doesn't make sense, rather than realizing they aren't good at communication.
because people's ability to communicate itself is biased towards culturally normal ideas, it biases their open mindedness, ability to learn, what they think sounds good, what they enjoy, etc, to culturally normal stuff. if they find something that's way better, that means it's different, so they have trouble with it. they often just get confused and assume it's bad.