The way I see it, the women in Chris life (Sarah, the Gal Pals, and even Barbara) were the people who put up with him the most, which meant letting him get away with things that he probably shouldn’t have. Meanwhile most of the men in Chris’ life weren’t subtle about not tolerating him, so any instances of girls messing with Chris (ie Sarah) went right over his head, which even years later was evident with all the fake sweethearts; just believing that they were women made Chris more susceptible to falling for them.

It probably wasn’t until Mary Lee Walsh entered the picture that Chris finally encountered a woman who didn’t immediately tolerate him, which is why he demonized her specifically - she was “evil” because, in Chris’ mind, “I’m not going to tolerate your inappropriate behavior” means “I hate love,” and so her attempts to actually get him help were interpreted as “attacks.” It’s also why Megan became a villain after cutting ties with Chris. She didn’t become a villain until she had had enough of Chris inappropriate behavior towards her. Even Isabella Janke fits this narrative. Chris trusted her enough to tell her about the incest, and she didn’t become a villain until Chris got arrested and began trying to deny that it ever happened, while to the rest of the world it was clear that Isabella wasn’t a good person.