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I think this proverb roughly means that a wise man isn’t lonely even if he is without company. However, when considering its construction, my understanding is starting to get shaky.

Let me explain what happens in my mind.

My daughter is no less talkative than my wife is.

My wife is (very) talkative. That’s true. However, my daughter might be more talkative.

The speaker wants to emphasize his daughter’s talkativeness.

A wise man is never less alone than when alone.

A wise man is lonely when he is without company. That’s true. However, a wise man might be lonelier.

Of course, I can’t understand my explanation at all. I’d be happy if you could tell me about its construction.

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  • Reminds me of Kipling’s “He travels fastest who travels alone.” Anyway, an extended expression of this idea is given by James Thomson’s poem “Hymn on Solitude”, which begins: /Hail, mildly pleasing solitude, / Companion of the wise and good; / But, from whose holy, piercing eye, / The herd of fools and villains fly./ … Here is the link: poemhunter.com/poem/hymn-on-solitude Apr 2, 2012 at 17:51

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I see where you're going with your interpretation, and you bolded the important parts of the sentence. I would parse the sentence as follows:

A wise man is not lonely when he is without company. However, he can be more alone than this. This means that, unless he is without company, he is at least or more alone.

This Cicero quote, borrowed later by Jonathan Swift, may confuse you because it seems contradictory. You parsed it correctly, but the meaning behind the phrase is along the lines of a proverb. One site explained that this means:

Wise people are resourceful and [do] not feel the lack of company when alone, because they can find plenty to think about.

That is, normal people would feel most alone when they are alone. Wise people, on the other hand, are the opposite because they may be able to find other things to cogitate on. People may or may not agree with this interpretation, but it suggests a reason why wise people cannot feel any less alone than when they are completely by themselves.

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  • I have to admit: the original took a couple of reads to parse correctly for me, but even after seven rereads, I still can’t parse your rephrasing! Oct 21, 2017 at 18:41
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I assume you're asking about the grammar; the basic sense has already been covered in the other answers. The cited example:

A wise man is never less alone than when alone.

has several negatives, a comparative construction, and a reduced subordinate clause. That's a lot of syntax to wade through. Moving the negative and restoring the markers unpacks it into something like this:

There is no time when (a man who is wise)ᴶ is less aloneᴱ than any time when heᴶ is aloneᴾ.

  • ((a man who is wise)ᴶ and heᴶ are tagged to make sure they're referring to the same personᴶ)

which, of course, makes no sense unless one interprets alone in two different ways:

  1. aloneᴱ, "Emotional" alone, means feeling lonely because of isolation.
  2. aloneᴾ, "Physical" alone, means actually being physically isolated from others.

And then the negatives turn out to be compositional, so they cancel out, and it resolves into

When (a man who is wise)ᴶ is aloneᴾ, he is less aloneᴱ than at any other time.

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  • I think you answer exactly what I’d like to ask, but, unfortunately, some letters turn into garbled characters, and my English ability is a little treacherous. Let me check with my understanding, if you don’t mind. The point is "never" covers two parts of the sentence (less, when-ever). Am I right?
    – user7493
    Apr 4, 2012 at 6:32
  • Not exactly. Never means "not at a time" and "whenever" means "at whatever time"; the thing is that there are two senses of being "alone" (the raised letters after "alone" are just Capital E and Capital P, for Emotional and Physical, and Capital J to mark various noun phrases as referring to the same person. Sorry). Anyway, never applies to being Emotionally alone, which doesn't happen, while whenever applies to being Physically alone, which does happen. That resolves the contradiction. And then the never and less cancel out and you get the sense I suggested. Apr 4, 2012 at 14:37
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    After so many years, the penny dropped. Thank you so much. I'm really happy thanks to you.
    – user7493
    Apr 5, 2012 at 4:33
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A wise man is never less alone than when alone

Wise people are resourceful and do not feel the lack of company when alone, because they can find plenty to do and plenty to think about.

It could also be taken to mean that a wise man might actually feel himself to be more alone in the company of other, less wise people (who he can't relate to), but I think that would be an unlikely interpretation. Though it is somewhat covered by You're never more alone than in a crowd.

Here's "She was never less alone than when alone" in The Scots magazine (1764), so the basic form has been around for a while. The repetition of alone, and the three consecutive "negatives" ("never less alone") make for an interesting wordplay, provided the sense itself can be successfully decoded.

The construction is only loosely related to "My daughter is no less talkative than my wife", which compares two different people, and doesn't involve anything unusual about the words or meaning.

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  • I see you found the same site I did.
    – simchona
    Jul 26, 2011 at 3:56
  • I wish someone with better reference facilities than me could establish for certain whether Jonathon Swift really was the originator, as claimed in a couple of sites. It just doesn't seem to me like the kind of thing he would have come out with. Jul 26, 2011 at 14:26
  • @FumbleFingers That’s an enlightening answer. Thanks!!
    – user7493
    Jul 27, 2011 at 4:18
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I finally cornered this once I realized the value of the word "never". Taken at absolute value you can convert the phrase "never less" to "always more" (actually "always more or equal to," but for wrapping your head around it, just call it "always more"); and there you go, now it makes sense: A wise man is always more alone than when he is alone.

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