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Look, this is all about integrity in your current position, not what you did or didn't do as a feckle youth and whether it was right or wrong. How many royal princes have dressed in Nazi uniforms, or prime ministers popped their knob into a dead animals mouth? The stuff we did when young can come back to clout us later in life, unless we declare it.
That's it, really. My difficulty was remembering it all for DV, in fact Positive Vetting the first time around in the 90's, so I added some pretty ones to the list too.
Being embarrassed about a mistake he made 20 years ago and not bringing it up is not lying to his employer.
Disclosing for vetting is being honest.
Unless his employer asks he is not lying to them, and its not necessary to give your entire life history to someone, even employers