Can you ever understand something you don't understand?

I never understood mens’ fascination with breasts. I tried.
Lets just call it the ‘level’ of fascination. Obviously standard attraction towards the opposite sex aside.

Certainly.

Yes of course, but it is hugely affected by how well it is explained.

Some things are intellectually understood and some things can only be absorbed through your deep place of your spirit. What kind of understanding or discernment is it?

Oh, absolutely. Sometimes all it takes is a slightly different explanation, maybe from someone who’s better at seeing things from a novice’s point of view. All too often, experts are so at ease with their knowledge that they have a hard time getting down in the mud pit of ignorance where we mortals wallow and giving us a boost up. It can help to read several different explanations of the same subject; sometimes one will just “click”.

In other cases, it’s just a matter of gaining more life experience. I’m probably less “intelligent” now, in my 50s, than when I was in my 20s, but I often find that when I revisit literature or philosophies that seemed quite opaque to me back then, I just “get it” now. That’s a matter of having lived through more, paying attention, and making connections along the way.

Sure. Some people call it an epiphany. If they have a word for it, it must happen occasionally. Right?

Of course. I can now do math that seemed like Greek to me a few years ago, for instance.

Sometimes you just need to be taught by the right person. Sometimes you need to learn a few intermediate concepts before you can understand that final goal. Sometimes (if you’re not an adult yet) you need to let your brain grow a little more. Sometimes you just need to think about it for a really long time before it clicks into place.

Wait. After rereading the question I see it can be interpreted as a Zen-like question .
The answer is No. You cannot understand something you don’t understand since the instant you understand it, you no longer don’t understand it. (Understand?)

If it’s not a Zen question then the answer is “yes”. There is still hope. You just need a better teacher who can help you find the right tools.

I’m speaking English now, aren’t I? Not some garbled cooing and giggly noises? Alright, then.

It depends.

I think it depends. Sometimes it never happens. ( i.e. the meaning of life)