Por favor dales mis saludos a tu familia.

English Translation

Please send my regards to your family.

I had expected dale, to conform with the singular familia.

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Agreed. I think this is a case where the speaker thinks of the family as a vague plural thing and the actual word only pops up in their head mid sentence.

You can also not have any pronoun in this case. ‘da mis saludos a tu familia’.

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