fun fact: on the Good Place podcast, Jason Mantzoukas said many of Derek’s lines were written by putting dialogue through google translate several times, which is definitely how they got this sentence.
so in the 800 times they got reset, there’s been some Chidi/Eleanor, some Eleanor/Tahani, and some Tahani/Jason.
So there’s… a non-zero chance that there was some Chidi/Jason going on at some point.
And to be honest, all I can imagine is, like, it’s a timeline where for some reason Jason kept quiet for a lot longer so Chidi finds himself attracted to this wise, calm, silent monk that just listens while Chidi rants about the problems he’s facing….