A Chinese philosopher, Lao Tzu, once stated “The journey of a thousand miles begins with one step”. Dante’s journey into hell, as he described in his many cantos, was undeniably critical to analyze; it was Canto II, however, that depicted his very first step. Dante did not only make Canto II his introduction to hell, but also implied the philosophy of Christianity in the canto. Numerous readings, including this canto, suggested that cooperation is highly emphasized in the Christian culture. Before setting out for the journey, Dante spoke cowardly to Virgil: “Poet, you who guide me, consider if my powers will suffice before you trust me to this arduous passage” (Inferno, 2.10). Clearly, Dante did not think of himself as a hero. Despite already having Virgil as a guide, Dante still lacked confidence and commitment. This confirmed that fact that Dante will unlikely tour hell alone; therefore, unable to reach the divine heaven. Here, I argued that he had intentionally done this to illustrate the Christian ideal that ones could not achieve one’s ultimate goal alone. Dante further completed this argument, as he informed his readers of his many other support characters; three of them, in fact, were from the heaven. Remarkably, the three aides did not only reside in heaven, but also came to Dante as a chain. When Beatrice encountered Virgil in the Limbo, she said she “heard of him in Heaven, [she] feared he has gone so far astray that arose too late to help him” (Inferno, 2.64).