RICHARD: And I am shocked by your naïveté … Did you really have pictures of Norman Rockwell family Christmases dancing in your head? Lorelai had her chance for a family, she walked away from it. That was her choice.
Norman Rockwell (1894-1978), painter and illustrator, most famous for the cover illustrations of idealised or sentimental American life he created for The Saturday Evening Post for five decades. His Christmas illustrations [pictured] are well known as iconic images of the Yuletide season, and still popular.
Richard also references the poem, “A Visit from St. Nicholas”, attributed to Clement Clarke Moore, and previously mentioned as a classic work which has shaped the American view of Christmas. In the poem it says,
The children were nestled all snug in their beds,
While visions of sugar-plums danced in their heads.
Richard mocks Emily’s hopes for Lorelai and Christopher to be together as idealistic and sugary-sweet as Christmas paintings and rhymes. He has never wavered from his position that Lorelai had one chance to have a husband and family, when she was sixteen, with Christopher, and that walking away from it was irresponsible. The idea that not marrying Christopher might have been the responsible thing to do, not to mention that stepping back from Christopher and Sherry now is the more moral choice, is something he cannot fathom.
The Annotated Gilmore Girls 