Not me saying this, but Will and Ariel Durant wrote the above sentence which caught my eye last night while reading one of their works*.
Do you think it’s accurate? Why or why not?
*(Volume 9 of their The Story of Civilization series, The Age of Voltaire, on page 299)
I’m sure it’s true. Men are simpler than women. I am a man though, a woman might hold the opposite opinion. Or maybe both men and women are clueless about each other. But I’ll stick with my initial response because I can understand why a lot of men are the way they are but I can’t say that for many women.
As a gross generalization, probably true. I’ve had women explain that they have to be observant about men in order to gauge how they might act. There’s also the thought that men might intimidate or harass them.
Men don’t usually have that need, so they don’t work to develop it.
It’s a cliche that men say they don’t understand women, but you rarelyt see the same cliche that women don’t understand men. That would reinforce the stereotype.
I think women are raised to pay attention to men in a way that men are not raised to pay attention to women. Somewhat superficial example: as a high school teacher, I will tell you it’s absolutely expected for girls to go watch their boyfriends play any Sportsball event, but not for boys to watch their girlfriends play. It’s just how it’s done. Boys are understood to be universally interesting, where girls are interesting only to other girls.
That sort of attitude pervades our culture.
I wonder is there is something else at play in addition. Boys think that their girlfriends are coming out to watch them play. I wonder if girls don’t insist on their boyfriends coming to watch them play because they think the boys will be looking at other girls?
Anything to that?
I think it’s true but poorly stated. Women (as a crude generalization, of course) are generally more sensitive to the subtleties of the state of mind of all other people, including other women.
I think this is most of it.
By extension, I think it’s also true that men tend to understand other men better than women understand other women.
In sum, it’s not so much about men’s understanding vs women’s understanding, but about the ability of anyone to understand men vs the ability of anyone to understand women.
That said, it’s probably also true that women tend to more socially oriented than men are and tend to put more focus on understanding other people than men do. So it’s likely that this is a component of it as well.
The problem arises when women look for depth that men just don’t have. If a man says he would like to order the fries, it isn’t a commentary on a woman’s cooking, or hairstyle, or weight, or fashion sense or anything else other than the fact that he is feeling peckish and would like to consume oily starch sticks covered in bits of rock. 
My ex-wife: ‘when you say you are thinking of nothing, I’ve come to realize you really are thinking of nothing.’
Even before the behavioral differences we are very different physically. Men don’t have to produce new men and women, we just supply half the config file and women have to do all the rest. And all the rest is quite a lot. That in itself requires more behavioral complexity than men need.
I don’t intend to oversimplify this, there are lot of discrete examples of behavior and biology to consider. But I think the prevailing opinion will be that women know men better than men know women.
I’m not sure this is really true except for men’s sports being more interesting than women’s sports. So the girlfriend would be expected to come watch football, basketball, baseball, or soccer but I’d be shocked if the girlfriend was required to come watch cross country or a swim meet. Back in high school I’d attend a girls soccer game and there would be 20 of us in the stands compared to the 5000 at a football game.
As for the general question in the OP ya, I think women understand men better than men understand women. I also think women understand men better than men understand men. Men just don’t pay that much attention to the deeper social stuff.
The number of times I’ve hung out with a buddy and then come home to my wife asking a bunch of questions about his life that never crossed my mind to ask beyond “do you think that was an out?”
I’m an exception to the rule - in fact, I’m not very good at reading anyone in general.
What do you suppose it means when a woman asks you if you’re going to order fries?
It took me quite a while longer than it should before I figured that one out.
It means she wants to share, of course.
No. It means she wants you to share your fries. Even if you were thinking about a baked potato. But then still, order a side of fries while she orders her salad.
No. That’s not the case. That’s not even a little bit the case.
Proving the OP hypothesis to be correct.
I think the lower-class person always watches the upper-class person more than vice versa. It matters more to them. And so women watch men more than men watch women.
I generally think that the assertion in the OP is true.
After years of being married I also came to the conclusion that women generally want to look good when they go out, not for men, but for other women. This conclusion does not hold true when women are dating or trying to catch the affections of men, but when women are in a confident relationship, it is definitely true. And there is nothing sexual here, it is more of a competition.
I think it dates back to before civilization. Being larger, men dominated women physically, Women had to out-strategize men, paying more attention to their thoughts and motivations.
I’ve heard the Mona Lisa’s “I’ve-got-a-secret” smile cited as an example.