In Canto 20 Dante grieves over the sinners who have to walk with their heads on backwards for the rest of eternity. For the first time in Malebolge, Dante feels pity for the sinners in this circle, and Virgil chastises him for his behavior. Perhaps Dante wasn't ready to see the true nature of sin in those earlier cantos. It's also possible that Virgil is fallible and can also feel pity for some of the souls in Hell but not for those in the final circles. However, it surprises me that someone else has to chastise Dante for feeling sympathy. My only explanation for this is that he can relate to the sins of these people and therefore, seeing them suffer for there sins is something he can fear and relate to as well, but not surprisingly, this weight of sympathy does not burden him for long.
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