On a recent episode of 'Gossip Girl', Blair evaluated how good a match she would be with Yale as her college: "I am so better fit for Yale than that Rory."
That was an in-joke, making a reference to Rory Gilmore of 'Gilmore Girls', who went to Yale during the course of her series.
But there was no mention in Blair's comment that 'Gilmore Girls' was a TV show. So it could be that she was referring to Rory as a real person.
The easiest splainin would be to say that she was referring to some other Rory, maybe even a guy named Rory. But I like the challenge of accepting it to be about Rory Gilmore.
I'm thinking that during an orientation visit to the Ivy League school in New Haven, Ct., Blair was introduced to Rory, who was acting as some kind of upper class mentor. And it looks as though despite Rory's best efforts, Blair did not cotton to her at all. And that, once having heard about what Rory accomplished while there, Blair probably saw her snooty self as being able to do so much better at Yale than Rory did.
So that Zonk should go directly to Yale and not collect 200 dollars!