Talk about something you did that made you feel ashamed of yourself afterwards.
Captain Jack Sparrow is shameless. If you are doubtful of this, just ask him. He will tell you. He will boast of it! Depending on his mood, he may dismiss the question with an airy, fey wave and an insouciant quip, or he may get expansive and wax eloquent (and perhaps a bit loudly) about the fact that pirates by nature are shameless creatures, freed from any and all societal constraints designed to induce shame in mere land-lubbing mortals such as yourself. Pirates do as they please, when they please, to whomever they please and damned be any who dare to get in their way. Pirates are the worlds only truly free men (and women) he will tell you, and the truly free are free of shame. Heaven help you, my friend, if he's had a few drinks in him when he's tell you this, particularly if you are a lovely young thing with whom he would like to take a tumble, because if he has then he will likely get poetic and point off into the distance and start to seduce you with words about freedom and horizons and endless possibilities, and no accountability, and seizing life by the horns and seizing the moment… and before long he will have had his way with you and then moved on, and you will both have been richer for the meeting.
At least, that is the romanticized view of piracy that Jack Sparrow believes in. He may steal from you, but he truly feels that he has done no harm and may actually have enriched your life. Where is the shame in that? If he tricks and flatters and wheedles his way into other people's fortunes, and manages to sack whole ports without firing a single shot, where is the shame in it? There is none. Except for one thing, Jack Sparrow feels no shame. That one thing haunted him for nigh onto ten years. Taking on the pirate Barbossa to be his first mate, knowing full well when he did so that Barbossa was a pitiless, cold-blooded murderer, that moment still fills Jack Sparrow with shame. He knew full well what sort of man Barbossa was, but he also knew that Barbossa was one of the finest sailing men alive, and Jack Sparrow needed the finest sailing men to sail to the Isla del Muerta. The night that he signed on Hector Barbossa to be his first mate, he told himself that it didn't matter that Barbossa was a treacherous, vile murderer so long as he was a good sailor, a good pirate. When Barbossa mutinied and stole the Black Pearl and left Captain Jack for dead, Jack did not know who he was more angry with, Barbossa or himself. But there was no mistaking the terrible sting of shame that he felt as he watched Barbossa sail away with his ship. He had betrayed his own ideals of piracy when he'd willingly brought that man aboard his ship. Ten years later he got back his ship and had his revenge, but the shame of it stays with him to this day.
At least, that is the romanticized view of piracy that Jack Sparrow believes in. He may steal from you, but he truly feels that he has done no harm and may actually have enriched your life. Where is the shame in that? If he tricks and flatters and wheedles his way into other people's fortunes, and manages to sack whole ports without firing a single shot, where is the shame in it? There is none. Except for one thing, Jack Sparrow feels no shame. That one thing haunted him for nigh onto ten years. Taking on the pirate Barbossa to be his first mate, knowing full well when he did so that Barbossa was a pitiless, cold-blooded murderer, that moment still fills Jack Sparrow with shame. He knew full well what sort of man Barbossa was, but he also knew that Barbossa was one of the finest sailing men alive, and Jack Sparrow needed the finest sailing men to sail to the Isla del Muerta. The night that he signed on Hector Barbossa to be his first mate, he told himself that it didn't matter that Barbossa was a treacherous, vile murderer so long as he was a good sailor, a good pirate. When Barbossa mutinied and stole the Black Pearl and left Captain Jack for dead, Jack did not know who he was more angry with, Barbossa or himself. But there was no mistaking the terrible sting of shame that he felt as he watched Barbossa sail away with his ship. He had betrayed his own ideals of piracy when he'd willingly brought that man aboard his ship. Ten years later he got back his ship and had his revenge, but the shame of it stays with him to this day.