His problem isn't just that he doesn't socialize enough though. Chris inherited very toxic views about other people from Barb, and his misadventures with trolls have made them worse. What I mean is, improving social skills isn't as simple as going from 1/10 to 3/10 (I know you were oversimplifying to make a point, I am too.) He might go out, talk to people more and more and learn to express himself more effectively, but that's not the only social problem Chris has. The problem isn't just that Chris is very shy and his autism has kept him from developing social skills on his own, it's also that he's an asshole. There's a bunch of reasons why he's an asshole, and it mostly isn't his fault, but an asshole he is, and that's something that needs to be deprogrammed before he goes out and socializes.
We see Chris (arguably) as he is: a pitiable man who has a hard time to cope, but Chris sees himself as a spunky internet celebrity whose only problem in life is a lack of girlfriend due to the interference of trolls. What's more, he's learned to associate concepts he finds uncomfortable with trolls and bullies, essentially allowing him to shut out anything he doesn't want to hear. That's all well and good when dealing with people online, but in real life, there's a diversity of opinion out there you have to cope with. I really think that before Chris goes out and socializes, he needs to work on the deep-seated personal issues that have been plaguing him since childhood. Right now, any social activity with Chris requires the other party accept Chris as he presents himself, which is why he socializes with internet trolls and mall cops. If Chris learns to accept himself as he is, maybe then he'll be able to socialize normally, and maybe he'll even get that girlfriend he's always wanted.
