I wouldn't be surprised if it turns out Chris is just in a constant loop of despair, being pulled in violently in two opposing directions by his addiction to frivolous spending, and his growing debts and responsibilities.
Here's the stages I think Chris has been going through in recent weeks.
* Chris is contacted by various companies, because he hasn't paid his debts
* He begins to panic, as he so often does when faced with real problems and consequences
* Starts to sell fucking everything, even going so far as to offer blowjobs for money
* Is willing to do literally anything for a few hundred bucks
* Weens flock to exploit this opportunity
* It's successful. After exploiting and jerking off everything and everyone around him, he's done it.
* Chris is relieved and wants to de-stress.
* He decides to spend some of the money on a new iPhone, and video games
* Chris either believes he can get more money out of his "fans" or he's got enough money for both the bills and new shit
* Suddenly he realizes he forgot about a bill, or forgot about food expenses, or Barb's medicine
* Rinse and repeat