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I hadn't waited long before he showed up.

is a common expression, but

I hadn't waited long until he showed up.

sounds strange. I wonder why. Is something grammatically wrong?

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Take these two sentences:

I waited for three hours.

I waited until he showed up.

"For three hours" and "until he showed up" both serve to define the duration of waiting. We can't use both, because we'd be defining the same duration twice.

We can add more information, we just can't do it using "until". Any prepositional phrase works fine.

I waited for three hours before he showed up.

I hadn't waited long when he showed up.

Note the subtle difference between "before" and "when". The preposition should logically match the verb tense: You waited in the past, before he showed up, and then finished waiting when he arrived. Or, his arrival coincided with the period of time you were waiting or had been waiting. (A lot of English speakers miss this concept, so don't worry too much about it.)

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