I have a number of problems with this. I suspect they explain a lot of the downvotes casebash has gathered (none of which, as it happens, is mine).
The writing style is windy and harder to read than it needs to be. I was going to attempt to help by rewriting it to be clearer, but ...
Many key points are left unstated and it's far from clear what's meant. A few examples: Is this really just about meanings of words? I think not; often both denotation and connotation arise from whole sentences or paragraphs. Is the claim you're arguing against "when reading anything, we should attend to denotation and ignore connotation", or "when reading anything written by rationalists, we should attend to denotation and ignore connotation", or even "when reading this particular thing I have written, you should attend to denotation and ignore connotation, and if the connotations bother you it's your problem", or what? Who are these "great deal of aspiring rationalists", these people by whom "the person who would object [...] is seen as acting irrationally", these "certain circles"?
Related to that last question: This feels like an attack on straw men. Again, who are these people who hold that one must ignore connotation and attend only to denotation? And, most especially, who are these people who not only hold that doing that is a good idea but who think that people who complain about connotations in non-rationalist settings "don't understand how words work" or "can't tell the difference between a denotation and a connotation"? I am not convinced that there are any. Well, one can always find a few people who hold almost any position, however crazy, so let me be more precise: I am not convinced that there are enough for there to be any need to argue against them. So this article has a bit of a "But I tell you the sun does rise in the east!" feel about it.
(Unclarity about who's being addressed is a major part of why the article is hard to read.)
If you think there is a genuinely widely held opinion or attitude here on LW against which you have a good argument, let's have examples. Show us someone saying that we should ignore connotations. Show us the context for this -- what connotations of what utterance(s) are they saying we should ignore, when, and why?
When a rationalist is engaged in conversation, it is very likely that they are seeking truth and that they want (or would at least claim to want) to know the truth regardless of the emotions that it might stir up. Emotions are seen as something that must be overcome and subjected to logic.
On LW that's often the case but not always. A discussion about akrasia might not only be about gathering objective knowledge that's true but also about personally overcoming akrasia. Coaching conversations are about more than just the search for truth. I don't think that it's good to say untruths during coaching conversations but the search for truth still isn't the main objective. The main objective is personal change.
There's an NLP axiom that goes: The “Meaning” of Communication is the Response You Get It's very empirical and following it is useful for coaching interaction.
When I have my coaching hat on, I often communicate in that frame.
Frank Herbert writes in Dune:
All the way to the arena, though, the Baron sat back among the armored cushions of his car, casting covert glances at the Count beside him, wondering why the Emperor’s errand boy had thought it necessary to make that particular kind of joke in front of the Houses Minor. It was obvious that Fenring seldom did anything he felt to be unnecessary, or used two words where one would do, or held himself to a single meaning in a single phrase.
There nothing wrong with expressing multiple meaning with a single phrase. In some enviroments I communicate like that and going for a single meaning would be limiting.
There a mode of talking that's about expressing what I feel as richly as possible. There the point isn't to find words that the other person will understand but to find words that I feel describe my experience well on a phemological level.
This article could profit from an introductory paragraph to explain what you are talking about. In particular, I'd find it helpful if you introduced the terms "denotational content" in contrast to "connotation".
This article aims to challenge the notion that the meaning of the words should and must be understood as the propositional or denotation content, in preference to the implied or connotational content. This is an assumption that I held for most of my life and which I suspect a great deal of aspiring rationalists will naturally tend towards. But before I begin, I must first clarify the argument that I am making. When a rationalist is engaged in conversation, it is very likely that they are seeking truth and that they want (or would at least claim to want) to know the truth regardless of the emotions that it might stir up. Emotions are seen as something that must be overcome and subjected to logic. The person who would object to statement due to its phrasing, rather than its propositional content is seen as acting irrationally. And these beliefs are indeed these are true to a large extent. Those who hide from emotions are often coddling themselves and those who object due to phrasing are often subverting the rules of fair play. But there are also situations where using particular words necessarily implies more than the strict denotational content and trying to ignore these connotations is foolhardy. For many people, this last sentence alone may be all that needs to be said on this topic, but I believe that there is still some value in breaking down precisely what words actually mean.
So why is there a widespread belief within certain circles that the meaning of a word or sentence is its denotational content? I would answer that this is a result of a desire to enforce norms that result in productive conversation. In general conversation, people will often take offense in a way that derails the conversation into a discussion of what is or is not offensive, instead of substantive disagreements. One way to address this problem is to create a norm that each person should only be criticised on their denotations, rather connotations. In practise, it is considerably more complicated as particularly blatant connotations will be treated by denotations, but this is a minor point. The larger point is that meaning consisting of purely the connotations is merely a social norm within a particular context and not an absolute truth.
This means that when the social norms are different and people complain about connotations in other social settings, the issues isn't that they don't understand how words work. The issue isn't that they can't tell the difference between a connotation and a denotation. The issue is that they are operating within different social norms. Sometimes people are defecting from these norms, such as when they engage in an excessively motivated reading, but this isn't a given. Instead, it must be seen the operating within a framework of meaning as denotation is merely a social, not an objective, norm, regardless of this norm’s considerable merits.