RICHARD: Oh Emily, I know I’ve done nothing but disappoint you these past few months, what with how isolated I’ve become and all the social engagements I’ve made you cancel, and all the friendships I’ve jeopardized. And you like order, you like lists, you like to know where you’re going or what’s coming. You like all things planned. And then suddenly I impulsively unplan our entire future in one fell swoop. Well, I couldn’t face disappointing you again. I couldn’t face telling you that I’d spoiled the plan. Not now, not at this time of year.
Richard explains to Emily that he couldn’t stand the thought of disappointing her with news of his retirement, especially not at Christmas. Presumably he was going to tell Emily his news by the end of the Christmas holidays, to explain why he was not returning to work.
Note that Emily loves order and lists, just like Rory.
The Annotated Gilmore Girls 