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Reverend Dimmesdale is the Ryan Gosling of the Massachusetts Bay Colony. (You just know those single Puritan ladies had a Tumblr devoted to him.) He's a brilliant speaker, a kind man, and a wise reverend. Oh, and he's also Hester's secret, illicit lover.
So how did this upstanding pillar of the community end up fathering a love child?
Actually, we don't know. We don't know one thing about why this apparently sincere, devout Puritan minister decided that it was a good idea to sneak off into the forest with a married woman. But we do know that he feels bad about it, so bad that his
inward trouble drove him to practices more in accordance with the old, corrupted faith of Rome than with the better light of the church in which he had been born and bred. In Mr. Dimmesdale's secret closet, under lock and key, there was a bloody scourge. Oftentimes, this Protestant and Puritan divine had plied it on his own shoulders, laughing bitterly at himself the while, and smiting so much the more pitilessly because of that bitter laugh. (11.8)
That's right: Dimmesdale whips himself at night, punishing himself for his sin. He's obviously susceptible to shame, and acknowledges that he deserves to be punished… but he doesn't want anyone else to do it for him. He'd rather punish himself. This also leaves open a question: did Dimmesdale create the mark on his chest himself, or was it put there by the Black Man (Satan), or did it emerge on his skin because of the struggle in his soul?
Dimmesdale may have a lot of good qualities, but he also has some bad ones, like hypocrisy and weakness. Hester may not recognize it, but Chillingworth does. He tells her, "his spirit lacked the strength that could have borne up, as thine has been, beneath a burden like thy scarlet letter" (14.16). In other words, Arthur can preach a good sermon about the consequences of sin, but he sure can't deal with them himself.
He even has the nerve to tell Hester that he envies her:
Happy are you, Hester, that wear the scarlet letter openly upon your bosom! Mine burns in secret! Thou little knowest what a relief it is, after the torment of a seven years' cheat, to look into an eye that recognizes me for what I am! (17.18)
In the end, this guilt destroys him. He's a weak man who sins and won't accept his punishment, and the hypocrisy eats away at him. Recognizing that death is imminent, he chooses to purify his soul at the last minute by confessing his sin publicly and revealing the scarlet letter A that has appeared on his chest over his heart. And in the end, he is strong enough to be grateful: "God… is merciful!… By giving me this burning torture to bear upon my breast! By sending yonder dark and terrible old man, to keep the torture always at red-heat! By bringing me hither, to die this death of triumphant ignominy before the people! Had either of these agonies been wanting, I had been lost for ever! Praised be his name! His will be done! Farewell!" (23.35).
We can't like Reverend Dimmesdale, exactly, and we can't quite respect him, either. But in the end, we do feel sorry for him.