LORELAI: [Headmaster Charleston]suggested setting up a meeting with a Harvard graduate, like a dinner or something. He even gave me the number of someone he knows.
RORY: An alumni dinner?
An “alumni dinner” is actually a dinner given for alumni of a university, not by an alumnus. Harvard holds several alumni dinners each year.
Headmaster Charleston seems to be talking about meetings for prospective students which are set up by institutions such as the Harvard Club – there is a Harvard Club for Southern Connecticut in Wallingford. My understanding is that these are official events, which at least a couple dozen of the best and brightest from each area attend at the same time – not just one student being given a phone number by their school principal, which seems incredibly sketchy.
After meeting with prospective applicants, the alumni association involved (such as the Harvard Club) will then meet with an admissions officer from the university, and put in a good word for the students they think would make great “Harvard material” (or whatever university it is). It sounds like privileged kids getting even more help to be accepted into university, but these associations are apparently very keen to increase diversity, and may advocate strongly for bright, successful students from a variety of backgrounds.
It almost seems as if Headmaster Charleston considers Rory to be one of these “non-traditional” Harvard applicants, who might benefit from some kind of assistance. I’m not sure Rory is actually that non-traditional, but in any case, I’m pretty sure the situation in this episode doesn’t happen in real life – and if it does, it shouldn’t!
Somehow we’ve gone from Rory being special and having the brains and hard work and tenacity to get into Harvard to Rory needing to be shuffled in the backdoor through some shady deal with a Harvard alumnus.
The Annotated Gilmore Girls 