RICHARD: Oh, I told him all about you and your grades and how well you were doing at Chilton. Well, of course, he insisted on seeing you. He wouldn’t let me off the hook.
RORY: But I haven’t applied to Yale.
RICHARD: Oh, I told him that you weren’t finished deciding, that you were being very picky. I think that made him want you even more. They can be very competitive, these Ivy League schools. He’s expecting you at three. Oh, look, it’s three now. Well, we timed this perfectly now, didn’t we?
While showing them the Administration Building, it transpires that Richard’s real reason for bringing Rory to Yale is to get her an interview with the Dean of Admissions, who turns out to be a good friend of Richard’s (shades of Chilton, where Headmaster Charleston was a good friend of Richard and Emily’s).
Lorelai is outraged by Richard’s manipulation, but he has a point. Lorelai has got a bee in her bonnet about Rory going to Harvard and nowhere else, and this was the only way that Richard believed he could give his granddaughter a chance to go to Yale if she wanted to. As he points out, Ivy League colleges are very competitive, and it would be easier for Rory to get into Yale as a legacy, because her grandfather went to Yale.
Although Emily didn’t know what Richard planned to do, she does try to defend him from Lorelai. She points out that if Rory got accepted by Yale, it might make her more attractive to Harvard, which I don’t think Lorelai would have thought of by herself.