He asked me if I had been with Jack.
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tenjingCould it be 'He asked me whether I was with Jack'I interpret that as reporting Are you with Jack?
tenjingHe asked me whether I was with Jack ...I can see this as the indirect form of either "Are you with Jack?" or "Were you with Jack?"
tenjingHe asked me whether I had been with JackI see this as the indirect form of either "Were you with Jack? or "Had you been with Jack?"