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“Should Christians experience regret?”
“Regret” is not a word that appears very often in scripture, though the concept is certainly there. Matthew writes about the regrets Judas had when he saw that Jesus had been condemned to death. Perhaps he saw his betrayal as an opportunity to cash in, but never imagined the Jews would be so successful in pressuring Pilate to carry out their wishes. Upon seeing that his betrayal had sent the Lord Jesus to the cross, he suddenly wished to dissociate himself from his previous actions.
