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The end of chapter 13 and the beginning of chapter 14 both reveal one of the biggest reasons the marriage would have never worked well: age. Chillingworth says:
"Dost thou remember me, Hester, as I was nine years agone? Even then, I was in the autumn of my days, nor was it the early autumn."
Yes, some say love is timeless, but how often really do we see people marry who are 20 years apart. This separation made it difficult for Hester to ever have found Chillingworth attractive.
Another reason is perhaps the fact that Chillingworth was a terrible old devil:
Old Roger Cillingworth was a striking evidence of a man's faculty of transforming himself into a devil, if he will only, for a reasonable space of time, undertake a devil's office. This unhappy had effected such a transformation by devoting himself, for seven years, to the constant analysis of a heart full of torture, and deriving his enjoyment thence, and adding fuel to those fiery tortures which he analyzed and gloated over.
Okay, so he wasn't a literal devil, but the point is that if Chillingworth acted this way never exposing his identity just to be able to torture Hester, imagine what he would have been like as a true husband. He would have found reasons to be mad about the simplest things and then played games. No one wants that relationship.
Another possible reason that their relationship may have never worked is the fact that Chillingworth was very devoted to his work. He references himself being quite the scholar and beneficiary of being able to help so many people.
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