DARREN: [on answering machine] I just wanted to let you know that I just finished going over Rory’s records here, and no shock, they’re perfect. Rory, you are tailor-made for Harvard. They’re lucky to have you. As far as I’m concerned, you should pack your bags. I’m gonna tell all this to the people in admissions and I’ll give your headmaster a call as well, so take care and we’ll talk again.
There is no way that the alumnus who interviewed a prospective student would tell them to “pack their bags” – there are many, many excellent students who aren’t accepted into Harvard, nobody can guarantee anyone a spot, unless something very corrupt is going on. This goes right up there with Headmaster Charleston telling Rory she deserves to go to Harvard, just after she’s discovered breaking into his office, no less.
However, this is a way to neatly tie up the episode and let the viewers know that Rory will almost certainly be accepted into Harvard, and all her application anxieties are at an end. Although Rory has work for the newspaper to complete, and Lorelai needs to do tasks for the inn, they elect to spend their Sunday hanging out together instead, as if aware that their time together is running short, and therefore more precious.