He was a good straight boy to begin with, but there was bad blood in him. Somehow, somewhere he got into the dark deeds that lead straight to Devil's work, just like marijuana leads to heroin; you think you can take them dark deeds and leave 'em, do you? Just save a few for your bad days? Well, now, we all have those bad days when you can't think for shit. 
As the world left him behind and he fell to Inferno he heard some sobs "Will you ever return? Will you ever return?" from his good girl. He was moving in a series of convulsive spasms, like someone with an epileptic fit, his face distorted and his eyes wild like a lassoed horse bracing his legs. But something kept pulling him on. And now he's picking up the skulls and making the circle in Inferno so that he might revisit Jenny on that holiest of nights Halloween. 
Virgil is there to guide him and introduce him to the three-ring-circus of characters. Satan has a good word for you, the Baxter Twins give a smile, The Rivers of Blood and the memory of her. 

My daddy used to always sing me a song when I was going to sleep:

 "Life is short,

  Life is shit

   And soon it will be over.

  Not a man

    Alive today

     That isn't going to hell."

He had a truly horrible singing voice and always started crying at the word "is".