SOOKIE: I’m looking for a guy that looks like a guy that you could be with, only I’m deducting seventeen years off his age and I’m adding an all-boys private school uniform and a Yankees cap.
Sookie is looking around for Christopher, until Lorelai points out Sookie doesn’t know what he looks like. It seems hard to believe Lorelai has never shown Sookie a picture of Christopher, but from the way Rory treasures an old strip of photos of Christopher and Lorelai, it appears they possess no photo of him.
Sookie explains that she’s been looking for someone Lorelai would go out with, but imagining him seventeen years younger and in a private boy’s school uniform. This may suggest that Lorelai and Christopher went to separate single-sex private high schools. In real life, there are no single-sex private schools in Hartford itself, but a few in the nearby surrounding suburbs and towns that Lorelai and Christopher could have easily attended.
I’m not sure why Sookie is mentally making him a teenager in a school uniform when he’s an adult though. Maybe she’s going to then mentally add seventeen years to his age?
She gives him a Yankees cap because that’s what Luke wears!
The Annotated Gilmore Girls 