In the hospital, Lorelai shows Christopher his daughter Rory, who is a newborn in the nursery – a clear parallel with Christopher showing her Georgia in 2003. Christopher says that Rory is “pretty”, which Lorelai firmly corrects to “perfect”, in parallel to Christopher saying Georgia is perfect in the present day scene, with Lorelai saying she is “beautiful”, but a “solid second” to Rory.
Although slightly insulting, Georgia literally is Christopher’s second daughter after Rory – it’s as if Lorelai is keen to remind Christopher that Rory comes first.
We already know that Christopher proposed marriage to Lorelai, and she turned it down – a point of conflict between she and her parents, and something Christopher continued to feel aggrieved about well int adulthood. In this flashback, we actually see the proposal. Christopher uncertainly says, “So, I guess we should get married”, and then the scene ends.
We never see Lorelai turn this half-hearted non-proposal down, but can understand why she does so. It’s hardly the stuff of romance, and it’s clear that Christopher doesn’t really want to, and isn’t committed to the idea. Richard’s plan of Lorelai and Christopher marrying and living with the elder Gilmores comes to nothing.
Apparently Christopher was only going to be given a job at Richard’s company once he was married, as that never happens either. Richard feels resentful about his “plan” not working out, and continues to blame Lorelai for that right up to the present day.
The Annotated Gilmore Girls 