I can kinda sympathize with his frustration over losing the Parrapa the Rapper contest, I remember almost wanting to believe there was some kind of conspiracy keeping me from ever having a chance with a childhood crush who friendzoned me and feeling kind of clingy about her, but I never drew porn of her or told her I wanted to rape her, and we're talking about things that happened when we were in 8th/9th grade, I was much younger than Chris when I went through this
When Chris tried to date his gal pals in high school, he took the Ls pretty well. He understood "Well, you can't win them all." He was not a virgin with rage, he just figured he needed to try again or try harder. Remember, back then he actually did try asking girls out. Noviophobia hadn't set in yet.
Even going into college, for a good part of his first year at least, he would ask girls out. We don't know how many, but from what we can tell it wasn't just once or twice. Chris though, experienced failure after failure.
If Chris weren't a retard, someone might have said yes at some point. While people mock Chris' standards from his attraction sign, they weren't exactly high either. His high school gal pals were all attractive by virtue of youth being the ultimate beauty-enhancer, but in the context of high school, Tiffany and Miranda were not exactly beauties.
I mean, look at this image, can you *honestly* tell me that -- not knowing that Chris was a tard -- you'd automatically think Tiffany was totally out of his league?
Given his history of failure, it's totally understandable that Chris would eventually stop trying the direct approach. In his autistic brain, noviophobia made sense. "I have a boyfriend" is what people would tell Chris to let him down nicely, and it happened *all the time*.
Attraction signs were his next tactic, and really from a strictly logical standpoint, without an understanding of human customs, they're actually a pretty logical approach to meeting someone. People have done it with billboards and it's not that big a stretch to get there from just the concept of a dating profile.
When EVERYTHING failed, and he didn't have the self-awareness to realize what was going wrong, when in his mind he was trying his best, a conspiracy isn't that big of a stretch. It's an understandable conclusion for someone who can't understand why they're failing when other men, who are not more attractive on a superficial examination, succeed.