It is a general truism that people with zero experience doing X are incredibly bad at figuring out how on earth to effectively cope with X. It isn't something intentionally malicious, but it can cause all kinds of problems. I recall reading about some group setting up a meeting to try to reach out to Jewish people in the community and scheduling it for a really major Jewish holiday the equivalent of something like Christmas. No Jewish people showed up for this meeting, the whole point of which was "We know so little about what Jewish people in the community want and need that we are soliciting their input and trying to build bridges, but can't even be arsed to check a Jewish calendar before blithely picking a date that works fine for non-Jews."
This is the sort of thing women routinely deal with that creates problems because having to explain to your boss that this is even a problem for you is such a huge and fundamental issue.
It was anecdotal, and I'm not going to reveal the identities or experiences of the women involved. The OP asked for experiences & advice, and so I passed along as much of the experience & advice as I could. If you (or any reader) finds it helpful, great; if you don't, well, ultimately you are the only one responsible for deciding whose advice you act on.
It's known as a stereotype. "Men who do not have career wives are trouble/red flags/misogynist pigs." Unfortunately, this stereotype appears to be perfectly acceptable on this board.
