I just ran into this quote

I choose my friends for their good looks, my acquaintances for their good characters, and my enemies for their good intellects. A man cannot be too careful in his choice of enemies. I have not got one who is a fool. They are all men of some intellectual power, and consequently they all appreciate me. Is that very vain of me? I think that it is rather vain.

what does "A man cannot be too careful in his choice of enemies" mean? does it mean "a man should be as careful as possible to pick his enemies"?


Heed this quotation by Sigmund Freud:

The Brothers Karamazov is the most magnificent novel ever written: the episode of the Grand Inquisitor, one of the peaks in the literature of the world, can hardly be valued too highly.


"cannot be too [adjective]" means "it is not possible to be excessively [adjective]". No amount of the quality is so high that it can be called excessive.

"one cannot be too careful" means that "no amount of precaution is excessive": in other words, one should be as careful as possible, and must never think "I am being too careful". (So yes, your interpretation is right).

Though this is an often used form, it is not an idiom in the sense of having some unusual meaning: it is a literal meaning. "Cannot be too ..." is simply the negation of "can be too". "You can be too careful" means that there is some limit where precaution becomes excessive, and "you cannot be too careful" is the straightforward opposite: there is no limit at which precaution becomes excessive.

Another way to express the same things is:

There is such a thing as being too careful. [There exists is a reasonable limit on being careful.]

There is no such thing as being too careful. [There is no limit on being careful; one should be as careful as possible.]

Negations of "too" limits are tricky, and likely a source of difficulty for learners.

One issue is that we often think of the negation of a "too" clause (where "too" means "excess", rather than "also") verb as being some kind of "not enough" clause. For instance, people will probably think of "we don't have enough money" as the opposite of "we have too much money". So "we do not have too much money" is tricky: what is that, and how is it different from "we do not have enough"?

But the bigger problem is that negated "too" clauses usually have a different meaning from a strict logical negation, or are ambiguous between the logical negation and that other meaning:

We did not have too much money when I was growing up

in fact means "we didn't have much money". The word "too" is just there for emphasis.

The sentence does not mean "It is not the case that we had too much money when I was growing up". Another example:

This song is not too long, is it. [Ambiguous: "this song is quite short", or "this song isn't excessively long".]

Which meaning applies depends on the context and the emphasis. For instance:

This song is not too long, is it? [Genuine question: is the song excessively long?]

This song is not too long, is it. [Rhetorical question: the song is not very long, as I'm sure you agree.]

In "one cannot be too careful" we have the strict logical negation: "It is not the case that one can be too careful". Still, the other meaning can be invoked with "not too careful". For instance, suppose we see John walk carelessly down the hallway with a full mug in his hand and splash coffee on the carpet:

John isn't too careful, is he. [John isn't very careful.]

To catch the nuance, you have to use clues from the context, and if it occurs in spoken language, you have to pick up clues from emphasis (like in the "song not too long" example).

  • Thank you. Wow! that is kind of complex. I got the meaning of my question. Also, I understand generally what you said. However, I think I need to study more on it on more examples to understand it completely. Would you introduce me some links so that I could study more on it? – Juya Dec 23 '13 at 23:32
  • Why haven't you put a question mark at the end of "This song is not too long, is it."? – Juya Dec 23 '13 at 23:36
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    @user43947 I didn't put a question mark at the end on purpose, because this kind of sentence ends with a falling voice, and doesn't sound like a question. An "is it" sentence can be a genuine question rather than rhetorical, in which case it sounds like a question, with a rising tone at the end. – Kaz Dec 23 '13 at 23:39
  • Thx. This is new to me as well. I need to work hard to improve my English. – Juya Dec 23 '13 at 23:54
  • An admirable answer, Kaz, more to the point than mine. But OP brings up a point about "can't be too careless" in a comment on my answer. I've answered, briefly and inadequately, but it really belongs more with your answer than mine, so if you want to address it here I'll delete my comments there and here. – StoneyB on hiatus Dec 24 '13 at 0:46

Wilde was famous for this sort of epigram, created by inverting a conventional expression or maxim—for instance, "Work is the curse of the drinking classes" or "The only way to get rid of a temptation is to yield to it".

In this case Wilde is taking aim at the platitude "A man cannot be too careful in his choice of friends", which expresses the notion that you should choose your friends from people of good character, because their virtue will encourage you to be virtuous and because your reputation depends on what sort of people you associate with. The corollary is that you may ignore your enemies, who will be those spitefully envious of your superiority. Lord Henry, on the contrary, claims to select his friends merely for their good looks and is careful to make enemies only of people who respect his intellect. Left unsaid is that such enemies will engage him on the highest intellectual level, and thus strengthen both his intellectual abilities and his general reputation.

  • Thank you. to tell you the truth, the structure still looks odd to me. but your explanation is very good. could you tell me what the last part "Is that very vain of me? I think that it is rather vain." mean? – Juya Dec 23 '13 at 23:14
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    @user43 - If it still looks odd to you, that's a good sign. That's by design – even us native speakers have to stop for a moment and think about a sentence like this one. As for the "vain" part, the speaker is simply asking a rhetorical question: "Do I seem conceited [to assume my enemies appreciate me]? I suppose I do, in a way." – J.R. Dec 23 '13 at 23:39
  • So I am happy that this is really complicated. thank you for your second help:) Thus "is that very vain of me?" equals "Do you think I look too proud?" – Juya Dec 23 '13 at 23:50
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    That's a good paraphrase, yes. – J.R. Dec 23 '13 at 23:54
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    @user43947 Aha - I am just now discovering where your problem lies. I think Kaz' answer better than mine for that. HOWEVER: your new example probably gets into a quite different use, where somebody says something to the effect of "Don't get stressed, it's OK to be a little careless, but you cannot (=should not) be too careless." – StoneyB on hiatus Dec 24 '13 at 0:43

There is also another aspect to intelligent enemies that is not well described here or otherwise. While the main POINT of the epigram is vanity. Having intelligent enemies is not just about having intellectual challenges, its also about class. An intellectual enemy will not throw themselves into mutually destructive or crass and brutal engagements. Tell me this, would you rather make an enemy of a 280lb drifter working at the docks, or a man of high society? One will engage you socially, the other will murder you.


The human being can select his/her friend,but he/she can not select his/her enemy.

Because you don't know who is or will be your enemy.

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    If you can "make friends", I believe you can "make enemies" too. I think it means what it said, you can't really be too careful or you have to be really careful (with your choice). In case you make enemies, you would want to be careful with your choice. Would you agree? – Damkerng T. Dec 23 '13 at 8:23
  • We talk about healthy and logical people .these people behave in a way that "makes friends" as they can. – mmb Dec 23 '13 at 8:29
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    Yes you can select your enemies; and the statement in fact says that: when selecting your enemies, you should be as careful as possible. When you plan your strategic moves in life, you can often quite easily predict about who might become your enemy if you make a particular move. Anyway, that's not the question. OP just wants to understand the English "cannot be too careful". – Kaz Dec 23 '13 at 19:31
  • Ideally, one would have no enemies at all, but in real life that is nearly impossible. If you must have enemies, make sure they are intelligent enough to know your strengths so that they will not foolishly attack you. – Phil Perry Jun 16 '14 at 15:37

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