Anonymous She had helped him since he asked to look after his sister. She had helped him since he had asked to look after his sister. Hi, To be honest, neither is natural to me.
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AnonymousShe had helped him since he asked to look after his sister.Hi,
She had helped him since he had asked to look after his sister.
Anonymous.1. ("since" + past tense): She had helped him since he left home.2. ("since" + past perfect tense): She had helped him since he had left home.If you have good reason for the past perfect in 'She had helped him' (and that is not clear from this single sentence), then the past perfect 'since he had left home' is natural and correct.