Nice Guy and Nice Gal are idealized gender roles for an optimal society.
I think we're talking past each other here. The "Nice Guy (tm)" phenomenon I was referring to is categorically not an idealized gender role within an optimal or any other society, hence the sarcasm trademark, although it has its roots in (a misinterpretation of) one idealized masculinity. Instead, it's a shorthand way of describing the pathology you described in the ancestor: the guy in question (there are women who do similar things, but the term as I'm using it is tied up in the male gender role) performs passive masculinity really hard and expects that sexual favors will follow. When this fails, usually due to poor socialization and poor understanding of sexual politics, bitterness and frustration ensue.
I actually think the terminology's pretty toxic as such things go, since it tends to be treated as a static attribute of the people so described instead of suggesting solutions to the underlying problems. It's common jargon in these sorts of discussions, though, and denotationally it does describe a real dysfunction, so I'm okay with using it as shorthand. Apologies for any bad assumptions on my part.
You might want to link “Nice Guy (tm)” in the grandparent to, er..., somewhere.
One of the lessons highlighted in the thread "Less Wrong NYC: Case Study of a Successful Rationalist Chapter" is Gender ratio matters.
There have recently been a number of articles addressing one social skills issue that might be affecting this, from the perspective of a geeky/sciencefiction community with similar attributes to LessWrong, and I want to link to these, not just so the people potentially causing problems get to read them, but also so everyone else knows the resource is there and has a name for the problem, which may facilitate wider discussion and make it easier for others to know when to point towards the resources those who would benefit by them.
However before I do, in the light of RedRobot's comment in the "Of Gender and Rationality" thread, I'd like to echo a sentiment from one of the articles, that people exhibiting this behaviour may be of any gender and may victimise upon any gender. And so, while it may be correlated with a particular gender, it is the behaviour that should be focused upon, and turning this thread into bashing of one gender (or defensiveness against perceived bashing) would be unhelpful.
Ok, disclaimers out of the way, here are the links:
Some of those raise deeper issues about rape culture and audience as enabler, but the TLDR summary is:
EDITED TO ADD:
Despite the way some of the links are framed as being addressed to creepers, this post is aimed at least as much at the community as a whole, intended to trigger a discussion on how the community should best go about handling such a problem once identified, with the TLDR being "set of restraints to place on someone who is burning the commons", rather that a complete description that guarantees that anyone who doesn't meet it isn't creepy. (Thank you to jsteinhardt for clearly verbalising the misinterpretation - for discussion see his reply to this post)