Head canon! the Squip saw the possible future where Jeremy defeated him ages ago but unlike the other pathways this would make everything in his life better, he'd get the girl, he would remain friends with Michael and get some new ones with the popular peeps, also his father starts being a dad again yay! So the Squip let it happen, all it needed to do was play the bad guy. A little silly I know but it's still my head canon, what do you think?
Oh that’s so damn sweet, it’s my head canon too now