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In Pirates of the Caribbean: At the World's End, Elizabeth Swan meets Bootstrap Bill at 01:18:18. In brief, Bootstrap realizes who she is, believes Will isn't coming to help him, and fades back into the wall. But then, at roughly 01:20:30, he suddenly sees her again and behaves like he doesn't remember talking at all.

Is this due to just old age or is there some specific reason related to the plot why Bootstrap doesn't remember the first convo?

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A part of the crew, a part of the ship.

Because he's becoming part of the ship.

The apparent death of his son Will Turner caused Bootstrap Bill Turner to sink into a state of madness, so much so that the process of assimilation into the Flying Dutchman accelerated, and Bootstrap's humanity began to wane. When Elizabeth Swann was thrown in the Dutchman's brig, she was able to coax Bootstrap into a conversation, though it was clear that he remembered little of his life. He still recognized the name of his son, however, and held on to the hope that William had promised to rescue him. When he realized who Elizabeth was, he lost hope for his own redemption. Bootstrap told her that Will would have to choose one of them and jokingly stated, "I wouldn't pick me." Elizabeth tried to wake him after he had merged with the ship again, but he appeared to have completely forgotten their prior conversation.

Some conditions of years of servitude under Davy James is that, at some point, one begins to grow barnacles and sea-creature attachments and then later, that crew member eventually becomes a literal part of The Flying Dutchman. In Bill's case, the process was accelerated due to his grief and loss of faith, believing Will was was dead.

As we see from the scene above (video), Bill Turner was about to become part of the ship when Elizabeth happens upon him and awakes him. He temporally snaps out of it, walks out of the wall, and talks to her as Bill Turner, but soon after forgets and repeats himself and begins to settle back into the wall of the ship.

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