Silver got mentioned in Shadow Generations lol.
So Gerald warns Shadow that he shouldn't say anything about the future, at risk of causing a time paradox. If he warned them about their fates (since they're from a time before the raid on the ARK), it could change Shadow's entire life... for better or worse.
Gerald is afraid of things going wrong if they touch the timeline, so he asks Shadow to just let things play out. It sounds like he has accepted that a tragedy is coming, respectfully treating the timeline as a sacred, self-regulating entity. But this big spiel about the nature of time reminds Shadow of Silver. He tells Gerald, and this is his response...
Gerald is like "well, that kid should really not be doing that" and moves on LOL. Makes me wonder if the games will ever touch on the repercussions of Silver traveling through time so much...
Anyway, don't overthink it. This is funny.
This reminds me when Shadow and Silver sealed Mephiles and Solaris, and this scene:
He did chose the lesser evil and Silver didn't argue.