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“Why dost thou smile so at me?” inquired Hester, troubled at the expression of his eyes. “Art thou like the Black Man that haunts the forest round about us? Hast thou enticed me into a bond that will prove the ruin of my soul?” (4.33)
You'd think that, if you sold your soul to the devil, you'd know about it—but here, Hester is trying to figure out if she actually did. Apparently, Chillingworth is so good as the whole creepy thing that he's actually being confused for the Devil.
As he spoke, he laid his long forefinger on the scarlet letter, which forwith seemed to scortch into Hester’s breast, as if it had been red-hot. He noticed her involuntary gesture, and smiled. “Live, therefore, and bear about thy doom with thee, in the eyes of men and women—in the eyes of him thou didst call thy husband—in the eyes of yonder child! And, that thou mayst live, take off this draught.” (4.13)
Does Chillingworth remind anybody else of the evil Queen in Snow White or of Yzma in The Emperor's New Groove? The interesting thing is that instead of killing people, Chillingworth keeps them alive. He wants Hester and Dimmesdale to be as healthy as can be so they can feel their punishment and the judgment of others as fully as possible. Even though he’s constantly being called the Devil in this story, Chillingworth is all about life and health.
"It was my folly! I have said it. But up to that epoch of my life, I had lived in vain. The world had been so cheerless! My heart was a habitation large enough for many guests, but lonely and chill and without a household fire. I longed to kindle one!" (4.18)
Aw. We could almost feel sorry for poor, lonely Chillingworth—except that he's about to prove himself a psycho-stalker.