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Wherefore henceforth know we no man after the flesh: yea, though we have known Christ after the flesh, yet now henceforth know we him no more. 2 Corinthians 5:16 KJV.

When could it have happened?

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    We are not told so we do not know. Saul was in Tarsus before Barnabus retrieved him so it is unlikely that he knew or saw Jesus. But who knows?
    – Dottard
    Mar 16 at 20:34

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What strikes me here is that Paul says "Christ" rather than Jesus.

When Paul says KATA SARKA ("according to the flesh"), he is normally making a distinction from KATA PNEUMA ("according to the Spirit"). E.g. Romans ch8 v5. In the first part of your quotation, he is talking about no longer knowing people in general KATA SARKA.

On that basis, I suggest that "knowing" people in this verse is about having or not having a merely human understanding of them. In that case it does not necessarily involve meeting them in person. He might know them only by reputation.

Paul knew Jesus "according to the flesh" when he thought Jesus was just another false teacher leading people astray. It was the Damsacus road experience that made it possible for him to know Jesus "according to the Spirit"; that is, to recognise him as Lord and Christ.

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