It is tricky, because the very people you are trying to understand are in no way obligated to teach you, and it's presumptuous to assume that they should.
This is something that a lot of people struggle with in trying to engage marginalized populations. That's why I said, it takes making it a priority, not just assuming that it should be reasonably easy to access understanding.
See I'm very comfortable broaching the issue of sexual assault, not just because I've been through it myself, but more because I've put in a lot of time in women's shelters.
There are ways to talk about vulnerable things, and it can take a bit to get to know the nuances, but like anything else, it's learnable.
You articulated my concern that I hadn't thought through enough to put down into words. The whole thing seems to be counter to a lot of what I read on here and in other venues about how other people don't owe you an explanation or as you said, it's presumptuous to assume people need to explain anything to you. I think it's an overused sentiment when it comes to a political or practical understanding of some issues, but when it comes to someone's personal trauma, I'm 100% behind it. That's why I was surprised that someone was espousing this belief and curious if others felt the same. Your point of doing research ahead of time is interesting and appreciated. I would very much like to explore those conversations because it's more meaningful than reading a random book about it - i.e. if you went to the same school as the person who you're talking to, you might know the people involved or remember the structure in a way that allows you to understand better how it could happen. Given all of the points people have had, I may be willing to bring up the topic if something ever comes up surrounding it in the future.
I also want to clarify - not to you specifically - but in general the other part of my comment about hearing other guys talk about things. After re-reading it, I wished I hadn't even said anything because it sounds like an arrogant, humble-brag, kind of odd and stupid thing to say about it. I just want to say that I said it because I'm kind of grasping at straws here. It's one thing to say that guys do stuff around women that men don't see, and that's why we don't know about it. I totally buy that. However, multiple people have commented that if you, as a guy, hear guys saying this kind of stuff, shut it down. Other guys have said, well, I was a part of this or that conversation where guys said, no means yes or wait until she's tipsy or whatever. I literally cannot ever remember a time in my life that anything this "rapey" has been said around me.
It's like when people commented on Trump's comments that it's just locker room talk. I've heard nothing remotely that crass outside of middle school/high school, and nothing about violating consent. The crassness level has only gone down as I've gotten older, and I can probably count on one hand, maybe two hands the things that I remember being around that I probably should have shut down in general because they were weird, gross, about an imbalance of power (boss commenting on subordinate women's attractiveness, etc.), but again, none remotely crossed the line into consent issues. I'm genuinely curious if I am the only one and was kind of throwing it out into the ether to see if others had any similar experiences (and if there's something personally to do beyond shutting down things that don't seem to be happening to me). I'm curious if I'm just fortunate to have friends that aren't that way.
You're not alone or at all unusual, a lot of men never directly see this shit. Men know who they can say flagrant crap in front of and who they can't, and you obviously give off the vibe that makes them not do it in front of you.
Make no mistake though, as I said above, it's almost guaranteed that you are or have been friends with men who do disgusting things, you just don't know it.
Also, it's entirely probable that you just aren't noticing the more subtle ways in which men mistreat women. The ways they interrupt us, talk over us, take credit for our ideas, treat us as if we are less intelligent, subtly try to impose their size on us, act "protective" when it's really controlling, objectify us but in a "polite" way, etc, etc.
This is where educating yourself and learning more from the women in your life will help you see things and understand them better.
You don't need to walk up to a woman and say "hey, were you ever raped? What was that like?". You can, however, have a friendly conversation with a woman and say something like "is it tough having all male bosses?" or "what's the gender parity like in your industry?".
If the woman isn't a coworker, then workplace gender dynamics are a good place to start in generating gender discussions with women because it's a big part of the popular discourse to discuss the glass ceiling, lack of female representation in senior roles, and the wage gap. It's not weird to politely broach subjects that are so widely discussed.
From there, if a woman wants to discuss different aspects of gender struggles, then she might choose to open up about it.
But look at what you've posted above about reading vs talking directly to someone. You talk about it being more "meaningful" if you know the people involved, but more meaningful to whom? Sure, it's more meaningful to you, but this isn't about you.
I guarantee it's more meaningful to ME if a man wants to take an interest in my personal experience with sexism and trauma if he's already well informed and well read on the subject. Otherwise he's not asking for my benefit, he's asking for his own education and bringing nothing to the table for me. It demonstrates nothing about understanding being a priority for him.
Meanwhile, if a conversation starts because I mention that I liked working in an all female environment, and the man is well versed in the issues facing women historically and presently, and he's clearly made it a priority to educate himself as to what half of the population experiences, then I'll feel like my experience actually matters to this person, and I'll feel understood and supported, which brings A LOT of value to me.
You also have to remember, if we're talking to a man who is completely clueless, we don't know how they're going to respond, and it can often be dismissive, condescending, or even hostile. So if you broach this subject without adequate knowledge, and the person doesn't already implicitly trust you, then they are likely to be on high alert because you obviously don't know enough to be safe from stupid responses like "well, you weren't in the room, how do you know she was raped, accusations like that ruin lives y'know".
So instead of approaching it with "how can *I* learn", instead approach it with "how can I provide value to this discourse?".