Meaning & usage
どんなに~(こと)か expresses strong surprise or deep feeling about degree, meaning “how very...” or “to what extent...”. どんなに comes at the start of a clause containing a verb, i-adjective, na-adjective, or adverb, and that clause ends in か, with ことか adding extra emotional emphasis as in 待ったことか or 心細かったことか. The か still has the feeling of a question about degree, often used alone as an exclamation or together with verbs of emotion or thought, and it cannot follow a bare noun, so a predicate is required.
Example sentences 7
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車の運転が出来たらどんなによいかと私は思った。
How I wished I could drive a car!
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もっと注意していればどんなによかったか!
How I wish I had been more careful!
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合格を知ってどんなに喜んだか!
How overjoyed I was to learn that I had passed!
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一人でどんなに心細かったことか。
How lonely and helpless I felt all alone.
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この知らせをどんなに待ったか!
How eagerly I waited for this news!
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母の料理をどんなに恋しく思うか。
How much I miss my mother's cooking!
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試験に落ちてどんなに悔しかったか。
How frustrated I was to fail the exam!
In past JLPT papers
This came up in 2 past exam questions.