"Ok, let's say I want to be a good person, and not cause offense to anyone other than the person I genuinely wish to insult.

What word can a man use to do this to insult a woman that won't offend?"

First of all, thank you for taking the time to work through this, that's the most important step.

Second of all, part of my point is that there is no handy-dandy list of prohibited words to refer to. It's always a judgment call, which means there's always risk entailed.

Personally, I think rather than focussing endlessly on trying not to offend the other person, a project that's doomed to fail at least some of the time, given that we come from different places, all are flawed, etc., we should instead focus on dealing with such offenses.

This was the crux of Obama's speech. He wasn't imploring us to never offend each other, for he knows this would be an absurd request. RAther, he called for us not to simply retreat to our corners once the offense has taken place.

That's the whole ballgame: what we do after and not before some offense has occurred.

The trick is resolving conflicts, not avoiding them. Of course, we should strive to achieve the former, but world peace depends upon the latter.

"There isn't one, is there? That's why I suggested using 'asshole', except I feel that most everyone would consider that term far more offensive when used to insult a woman than the word 'bitch', but they wouldn't be able to say exactly why."

Yeah, again, I can't help you. It's a judgment call.

"I mean, it's clearly not sexist, right? But at the same time, in this culture, at this time, the word 'asshole' is considered too impolite for a man to use in describing a woman."

I know. It's hard to keep up. No one said maintaining a civil society would be easy.

"What's the end result of this? That we can't use bad words to describe Hillary Clinton at all? How about Ann Coulter? She's a much bigger asshole, you know."

I don't know. Good question.

"So if you're going to go putting certain words out of the range of polite conversation, you really have to tell people the PC equivalent, otherwise you risk being ignored altogether, don't you?"

AGain, simply supplying people with a list of prohibited words is not the point. With all due respect, demanding such a list is a little bit lazy because it absolves one from the responsibility of having to be present in each and every interaction, of being sensitive to the power of one's words, the orientation of one's audience, etc. It requires a certain fearlessness, a certain embrace of the unknown and constant willingness to learn and adapt, as the situation requires. Yes, it's exhausting, but I'm not sure there's any shortcut available.

"Of course, I have similar issues with the word 'Asian'. Apparently the word 'Oriental' went right out some years ago, even though the word, literally, only means "Eastern", and instead, the replacement, inoffensive word cedes an entire continent to only one of the races that live on it.

I'm afraid I know too many Indians to be altogether comfortable using the word 'Asian' to describe a racial type. Russians, too, although I suppose Russia may technically be part of Europe.

Now, you might say that I have no business ever describing anyone by race, but here in the real world, everybody does it all the time, without being insulting or perjorative."

Of course. Again, I have no pat answer. It all depends on the situation.

"What word do women use when insulting each other. To their face? Behind their backs?"

I'm not a woman, but as far as I've gathered, lots of women use the word 'bitch' very readily.

"Not trying to be a jerk. Please tell us what word to use, and we'll use it."

I appreciate that you're not trying to be a jerk. Thank you for that.

Again, it's not a question of just memorizing rules about what to say and what not to say. It's about cultivating the sensitivity to the situation that would allow you to at least recognize all the possible ways your words might be taken, despite how you might mean them. You take your best whack at it from there.

I hope this is at least moderately helpful.

None of this is easy, and none can be solved on a blog, but some of the groundwork can be lain, which is something.