DEAN: What happens when you leave?
RORY: When I leave when?
DEAN: When you leave for Harvard . . . do we break up?
Rory acts as if Dean is being unreasonable to ask this question, but it doesn’t really seem so. After all, Zach and Liza broke up when they left Hartford to attend different universities. A lot of young couples break up when one or both go away to college, being realistic enough to know that long-distance relationships don’t usually work out for teenagers.
It does seem a bit premature to bring it up already – Rory hasn’t even applied to Harvard yet, let alone been accepted. It also comes out of the blue, as the pair of them were kissing, holding hands, and smiling together just seconds previously.
It feels as if Dean is either trying to ruin their last year together, or is pushing Rory for some kind of commitment. He must be feeling pessimistic about their future together, and probably rightly so, when they are headed in very different directions. I do sense a jealousy and possessiveness from Dean in regard to Rory’s education, as if it is taking her away from him.
The Annotated Gilmore Girls 