RICHARD: You know, one day, when your mother was ten years old, she ran into my office and she said, “I’m going to go to Yale, just like you.” She actually took my diploma out of my office and put it in her room. She wouldn’t give it back to me for about six months.
Rory learns from Richard that Lorelai’s original dream for college, was not Harvard, but Yale. This was when she was ten years old, and presumably before her teenage years drove a wedge between father and daughter.
Richard’s point could not be clearer – if Rory is hanging onto a dream of going to Harvard to fulfil what Lorelai wanted, then that wasn’t even Lorelai’s original plan. And if Lorelai changed her mind, then Rory can too.
The Annotated Gilmore Girls 