Verified answer

Dante passes out from pity twice in the first six cantos.

After Canto IX, Dante begins sassing off to Virgil. It happens in Canto XI, then again in Canto XXVI, and also in Canto XXIX. You get the idea. He’s not rude, but his "yes, sensei" attitude is gone. Along with his parallel development of the habit of blasting sinners instead of crying with them, Dante is gaining confidence in the words exchanged with Virgil. However, Dante’s ********* towards his teacher seems to do both men good, because they slowly grow more open in calling out each other’s faults or lapses of judgment.

By the end, it’s clear that Virgil still has the greater encyclopedic memory than Dante, but Dante student has learned a lot. Might there be reason to suspect that he surpasses his master morally?

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