CHRISTOPHER: Now it’s totally your call and I don’t want to step on any plans you’ve already made, but I know Rory has a break in school coming up, and I was wondering if you’d be cool with her coming to visit for a couple of days.
Christopher finally shows some interest in his daughter, inviting her to spend a couple of days of her Christmas break with him in Boston. The fact that he mentions Sherrie had fixed up the spare room for her suggests that it might be his girlfriend encouraging him to make contact with Rory.
Although Lorelai said she’d always left the door to Rory open for Christopher, she doesn’t sound thrilled with this plan. She never seems to have considered it might mean leaving the door to Rory open for another woman as well.
Note the picture on the wall of the ominous all-seeing eye and the word OBEY on it – does Christopher feel as if he is under Sherrie’s surveillance, that he is doing her bidding? Is the phone call something she instructed him to do? It’s a hint that Christopher may be finding his first committed domestic relationship rather confining.
(I’m not sure, but I think the artwork might be by Shepard Fairey, a graphic artist and founder of OBEY Clothing who emerged from the skateboarding scene in the mid-1980s. He would later become well known for his picture of Barack Obama together with the word HOPE).
The Annotated Gilmore Girls 