This is one of those comics in which I find myself not entirely sure what to say. This is MOSTLY because the next comic is so closely related that it feels like the second half of it, so I'm stuck here basically trying to comment on an incomplete thought.
Still, there is something worth noting. Another reason Jerry could have missed a difficult to spot affinity was because he had "one foot out the door", so to speak. He'd already started the process of ending his previous life and beginning the next. It's entirely possible he wasn't at 100%.
My point being THERE ARE NO PLOT HOLES EVER SO THERE