Most people in Chris' position would, after a while, be able to put two and two together and realize that the only girls who have ever shown a romantic interest in Chris have been trolls fucking with him and would be able to come to terms with the probability that he will never find a romantic partner, except for maybe a chick with similar cognitive impairments and looks as Chr8s does. Not Chris though. Until bare, undeniable proof is thrust upon him and he is forced to acknowledge it, every girl who throws themself upon him are totally real and he's finally found love.
Whether it's Autism, below normal intelligence, plucky optimism, or something else, there is something in Chris brain that is damaged to the point that he's not able to realize "Hey, the only girls who have said they want to be in a relationship with me have all been trolls trying to screw with me. Maybe I need to try to be less gullible and be more sceptical when a seemingly cute girl tells me she loves me."
However, JQ may have finally driven it home that he's probably never going to have a real loving relationship. He seems to be under the impression that Jessay was his last hope for having love and romance. I'm sure it won't stop him from creeping on girls and pining for a cute girl to call his own, but he may have finally been broken of that optimism that some girl is going to drop in his lap from out of the blue and ask him to date her. I could be wrong, but that's how it feels to this dude.
I hope not. There was some funny content from Jessica, but mostly it was just boring.
I'd like to think that, but I also thought that when the Catherine saga happened, and when Jessica came along. He often appears to have learned from his mistakes, but then he'll make them again. It's like he thinks, "Well, it didn't work out that time, but that was two years ago. Things might have changed."
Chris never has, and may never initiate with a woman. I think that he is still under the same old assumption/hope that girls will always be the initiators, no matter how unhygienic/idiotic he looks or how lowly his current social/economic status is. This is why he thinks nothing about how it's weird that women suddenly appear to him online and try to date him, his thinking here is to never look a gift horse in the mouth.
This will always be Chris's biggest weakness when it comes to trollsonas.. Sure he has gotten better at not completely letting them in until he checks, but once they get that "in" and bypass his checks, then it's completely smooth sailing.
As far as we know, he still didn't try something like speed dating at a bar or some other shit like that, despite him overcoming his original objections to those things (For example, alcohol). he just builds online social profiles everywhere and waits..
Remember that in his mind, he has no real life rejection experiences that were not troll influenced. To him, one of the biggest reasons for the failure of his overtures to Megan is the ED page, similarly, he cannot process the Wallflower's rejection of him without considering Surfshack Tito as a main factor in it.
The other times he was rebuked was entirely through Trollsonas. So that is invalid in his mind on principle.
IMO, the time we truly know that Chris has passed this issue is when we hear of him landing a date IRL through his own initiative. Which given his current state of mind, looks & finances is pretty much impossible..
Jessica Quinn is gone for the moment, so someone else who she was keeping at bay slid in and is trying to take over.
A trick like that works.
Once.
Jessica is not a troll in Chris' eyes right now. And I believe she'll come back again, like how she broke up with him over the Doopie thing.
But yeah, when Jessica is good and done with Chris, the Jessica Quinn trick won't work anymore.
The troll heist never changes, only the inflitration methods do.
And yes, Jessica will probably return at some point.