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In The Scarlet Letter, how does Chillingworth discover Dimmesdale's secret?

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Chillingworth discovers Dimmesdale's secret by observing his deteriorating health and behavior, leading him to suspect Dimmesdale's guilt. Chillingworth confirms his suspicions when he sees a scarlet "A" engraved on Dimmesdale's chest while he is sleeping, revealing Dimmesdale as Pearl's father and Hester's lover.

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He doesn't know for sure, at first.  But as he spends more and more time with Dimmesdale, he notices symptoms that lead him to conclude that Dimmesdale is tortured with something.  He is sickly; he flushed often; he is quiet and pained; he has strange injuries.  All of these things lead Chillingworth to conclude that Dimmesdale is not emotionally well.  He is burdened with something, and since Chillingworth is on the hunt for the man who has not confessed to adultery with Hester , he draws conclusions.  He hopes.  He suspects that Dimesdale might be the one. So, he spends more and more time with him, and watches and observes him closely.  Pretty soon, he is the reverend's personal physician, and even moves in with Dimmesdale as his health falter.  In their conversations, Chillingworth desperately and subtly tries to get Dimmesdale to slip up, to reveal something, or perhaps...

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to even confess his crime, to no avail.

It is while Dimmesdale is sleeping one night that Chillingworth's supsicions are confirmed; he looks at the sleeping Dimmesdale, and sees something on his chest that verifies he is indeed the man Hester had been with.  There, on Dimmesdale's chest, is an engraved letter A, cut into his skin and scarred over.  Dimmesdale, wracked with guilt, had been trying to purge his guilt by tatooing a letter A in his own chest.  He was "confessing" to God and himself and trying to make up for his sin in his own way.  This confirms Chillingworth's suspicions that Dimmesdale's awful secret is that he is Pearl's father and Hester's lover.  I hope that those thoughts helped; good luck!

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In The Scarlet Letter, why does Dimmesdale seem to hide something from Chillingworth?

In Chapter 10 of "The Scarlet Letter", Chillingworth already suspects Dimmesdale of being the father of Pearl and he is digging, trying to find out if he can coax the truth from the minister. Dimmesdale seems to be hiding something because he his the father of Pearl and does not want to admit it to anyone. In a conversation about hidden sin that is filled with innuendo and double meaning, Chillingworth taunts Dimmesdale . The minister says,"that the hearts holding such miserable secrets as you speak of will yield them up, at that last day, not with reluctance, but with a joy unutterable.” Chillingworth then asks "“Then why not reveal then here?”  This makes Dimmesdale very uncomfortable and he clutches his chest and answers, "So, to their own unutterable torment, they go about among their fellow-creatures, looking pure as new-fallen snow; while their hearts are all speckled and spotted with iniquity of which they cannot rid themselves.” Chillingworth is quick to observe, "such men deceive themselves!” Dimmesdale quickly changes the subject to the state of his own health. "He{Dimmesdale] had a ready faculty, indeed, of escaping from any topic that agitated his too sensitive and nervous temperament.—”But, now, I would ask of my well-skilled physician, whether, in good sooth, he deems me to have profited by his kindly care of this weak frame of mine?”  Then they are interrupted by the sound of Pearl's laughter.

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Dimmesdale has developed the habit of holding his hand over his heart and pressing it. He does this while speaking with Chillingworth. Later, Chillingworth looks under Dimmesdale's shirt while the minister is asleep (or drugged). We don't know what he sees, but it fills him with sadistic joy. Some readers have speculated that Dimmesdale had carved the letter "A" into his flesh over his heart and wore it much the same as Hester wore her letter, except his was hidden whereas hers was on public display. This would be consistent with his habit of whipping himself to alleviate his guilt. Some think that the letter appeared mysteriously.

Dimmesdale's gesture can be taken both literally and figuratively. He held his hand to his heart because he was suffering such guilt for his secret sin, or he held his hand to his heart because he was branded with his own scarlet letter. In either case, Dimmesdale did indeed have much to hide.

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