Remember in season two when Rory sits for that horribly awkward oil portrait that Emily gives Richard for his study? Shudder. But despite how weird it is for Rory, it's just the kind of thing Richard would love because of how much he cares for Rory — and Rory cares deeply for him, too, which is why she goes through it all. Since the show doesn't spend too much time in Richard's study we don't really see the painting again after it's done — until it pops up in the final episode of the revival, when Rory goes to her grandparents' house to write her book. Rory finds the perfect place for inspiration in Richard's study, and the portrait in the background seems like less of an embarrassing reminder and more of a callback to how close Rory and Richard were. Sniff.
