I’ve lived as both a man and a woman/trans woman. (MTF trans, I don’t know exactly what it’s like to be a woman, but much more than the average guy). Yes, there is no doubt than men typically have absolutely no idea what it’s like to be a woman and how women think and feel. In so many ways! Here are few briefly off the top of my head, from my experience becoming a woman:
- We like to express our feelings, and we’re often ignored. This is probably the most essential part of communications, and they don’t want to hear it often, or don’t listen and respect it. It was actually worse when I was a man, because as a woman at least I’m not immediately shot down and humiliated by other guys for having feelings
- I’m less invisible. By a HUGE margin. People are MUCH more interested in me, it’s easier to engage with people. Maybe it’s because I’m trans, but I don’t think women understand how hard it is for a man to get attention, unless he’s really good looking or loud and obnoxious
- It’s harder to just relax and walk around without people staring at you or bugging you. And yes it’s less safe - something guys are totally clueless about). But there’s a flip side, which is at least you’re not ignored almost all the time. Many more opportunities present themselves. I’ve been lucky and have rarely been outright harassed
- It’s harder for people to take you seriously on important topics. Engagement is more socially oriented. When I change the subject to a serious topic, you can feel the air deflate in the balloon.
- It’s incredible how much more joy there is in connecting with people when you get out of your head and are vulnerable.
- Plenty more (I wrote a book about it)

One powerful way for men to understand women better is to BE a woman for a while (eg dress as woman, go out a bit). That’s a pretty tall order, but I don’t know a better way.

Before I more fully transitioned, I went back to being a man dating women for a while. What a difference when I had a better understanding of women! I was more connected with them, more relaxed, it was more fun, I appreciated them more, I felt more empathy, and I actually really enjoyed sexually pleasing them much more!

And there is a flip side. Women don’t understand men, and if they did, things would be even better. But I sadly discovered that women pretty consistently have no ability or inclination to understand men. I think it’s because they think they already do, or think men don’t deserve it because they’ve definitely had much more privilege. It’s true that many men are as shallow as you think, but most are not. There are so many invisible great men out there, too bad so few women will ever know that. And some of these guys could use a great partner to help them, and many women could use a great partner to help them too. Sadly, the number of lost opportunities is too great to count.