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An English study book says, "He is less stupid than I thought he was is better expressed by either He is not so stupid as I thought he was or He is cleverer than I thought he was.
The book does not explain why they are considered as better expression.
Instead, it lists some more sentences of a kind and ask the readers to reword them as suggested because they are not good ones.
For example,
My mother is less old than you think she is.
These grapes are less expensive than those.
A donkey is less beautiful than a horse.
Would please tell me why "less ~ than comparison" is not regarded as good expression? Is there any grammatical background?
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HI Myid,

"He is less stupid than I thought .... " Well, this is not quite what natural English would sound like.

I would say it this way:" He is smarter than I thought..."

My mother is younger than you think she is.
These grapes are less expensive than those - OK, but also you can say "cost less"

A donkey is less beautiful than a horse. Ok, but also can be "less appealing".

Less old can be expressed "youger"

Less stupid can be expressed as smarter or brighter.
Thank you for your reply.
However, as a foreigner learning English, I need a certain explanation why some sounds natural and others does not.
Otherwise, it is very difficult for me to tell when I can use "less ~ than" and when I shouldn't.
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Hi myid, and welcome to the forums.

In general,

is less [adjective] than...

can be

She is not as [adjective] as... (As an American, I say "not as X as" but I think in BrE it's "not so X as")

She is less old than you think = She is not as old as you thiink.

These are less expensive than those = These are not as expensive as those.

A donkey is less beautiful than a horse = A donkey is not as beautiful as a horse.

You don't need to find any antonym like "younger" or cheaper" or "uglier" to make it work.
myid, I need a certain explanation why some sounds natural and others does not.

I believe that "natural" goes along with being "native" and defies logical explanation.

In your original, I feel that "less stupid" implies that he is, in fact, still stupid, and not very complimentary. "More intelligent" is just a little more positive in its approach.

Dear Grammar Geek,

Thank you for your answer.
I am not asking how to change "less ~ than" structure to "not as ~ as"
My question is;
1) "less ~ than" is not a good expression as the book says?
(perhaps not generally but in certain situations or with certain adjective)
2) If so, why is that?
3) Is there any rule when I need to avoid "less ~ than" expression?
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Thank you Philip.
May I understand this way?

He is less stupid than you think he is. -> offensive
He is not as stupid as you think he is. -> less offensive
He is smarter than you think he is. -> the least offensive
As Philip said, it defies a logical explanation. Of your examples, the mother one sounded odd, and the donkey one a bit odd, but the grapes sounded just fine.

However, in all of them, the "not as X as" would sound fine, so it's safe to use that construction until you have a feeling for the others.
Imid,

I need a certain explanation why some sounds natural and others does not.

I don't want to dowse your enthusiasm. Beside a persistent learning attitude, it will require constant usage and exposure to English to get a sense of what sound natural. I only say this.

Generally speaking, words have carry positive and negative elements.

If I say "John is a lot less confident and capable than I originally thought". I am saying expressing a message with negative element with positve words to minimize the impact. In reality, I am more disappointed in this performance. In this sentene, I am using a key negative word with a positive intensifier.
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