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First, I am not sure whether it is grammatically correct (that would be my first question) and I would like to know whether it is a normal usage or I should rather avoid that:

I heard he likes gambling. I will lend him the money unless it is true.

I heard he quit gambling. I will lend him the money unless it is not true.

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  • Grammatically there's nothing to stop you using unless + negation as per your second example. But it's stylistically clumsy - most people would avoid the pointless circumlocution by just saying I will lend him the money if it is true. Commented Oct 3, 2018 at 13:13

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They are both grammatical, but the sentences are too awkward to be spoken. The 2nd is more confusing than the 1st.

The negators (unless, not) come late in the sentence, and are likely to be missed or misunderstood by a listener because the beginning of the sentence seems like it is leading to a positive statement "I will lend him the money…" so the listener must shift gears at the end to reverse direction.

A natural way to say it would be:

I heard he likes gambling. I won't (will not) loan him the money if it's true.

I heard he likes gambling. I will loan him the money, but not if it's true.

This makes your concern about gambling, and the conditions of the loan, clearer.

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