I wanted to say Chris gets arrested by reports of "preying" on women in public restrooms. But Virginia doesn't have a bathroom bill, and Chris can pee as he wants.
Someone offers Chris his own website again. That or he makes a tumblr. Like in the past, his web design skills are lacking and he will leave vulnerabilities in his code, sometimes causing things to not work at all.
Barb dies, Chris does not notice, nor does he show any sign of grief beyond a sigh. We are not made aware until she is found in her bed or chair and a status is made for asspats.
Someone, or the site collectively, sends Chris a care package. By some sheer luck he will actually find the forums and start posting in his forum, sighing and going full autism on the fly. We end up having to either ban him or hide the forum like ADF. This is unlikely.
Barb dies, Chris finds himself homeless. Sometimes we will see him in real life lumbering the aisles of a toy store, trying to haggle the cashier with comic appearances. His tugboat won't afford him a place to live because it is spent on toys. Chris becomes forgotten and dies alone.
Jessica feels sympathetic for Chris and takes him in, post Barb death. They eventually date, and Chris goes public about EVERYTHING they do together behind closed doors. They marry, and Jessica becomes pregnant. Realizing Chris actually is a worthless piece of shit at long last, she divorces and kicks him out, and throws away all his toys. Neo-Chris is born into the world, and the saga continues.(If this happens, I'll be the one shitting myself)