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When we place a negative word before expressions like bore to death, does it negate the word bore, therefore making boredom non-existent? Or does it negate the whole expression, making boredom slightly existent? Or does it all depend on context, and the intention of the speaker? For example, If I said:

The teacher taught me how to solve math problems with fun. He didn't bore me to death.

Does it mean: He didn't bore me at all? or does it mean: He slightly bored me but not as much as, say, the other less-experienced math teacher who typically does.

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    I think you meant in a fun way (not "with fun"). Also, if it was actually fun, then 'he didn't bore me at all' or 'he didn't bore me to death' ('as I had expected' implied). – KannE Nov 1 '18 at 6:55
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Strictly as written, we cannot determine whether the person was not bored at all or merely bored a less than lethal amount. The particular meaning depends on context and on emphasis.

He didn't bore me to death.

Someone else may have bored the person instead.

He didn't bore me to death.

This is similar to the version without emphasis. We can't really tell whether the person was bored at all, but it would be reasonable that they were not bored.

He didn't bore me to death.

Maybe he did something else that was lethal.

He didn't bore me to death.

Maybe he bored someone else to death.

He didn't bore me to death.

The emphasis would likely imply that there was some boredom, just not a lethal amount.

The same sentence can be understood rather differently depending on the context or emphasis.

To disambiguate the meaning, we would need to make the sentence more explicit, such as:

He bored me, but not to death.

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