JESS: It’s not the first time a couple’s broken up.
RORY: It is for us.
In fact, Rory and Dean broke up before, in “Star-Crossed Lovers and Other Strangers”. However, as they got back together again, Rory might think it doesn’t count, and was only “being on a break”. It’s interesting that she doesn’t share this detail with Jess, as if not wanting to expose the cracks and weaknesses in her prior relationship with Dean.
The Annotated Gilmore Girls 
Oh, this had annoyed me ever since it aired. It so isn’t the first time they broke up, it’s the second! It still irritates me every time I watch that scene.
I have never considered that Rory may have retconned the breakup to being just a break, though. Huh. I have just always blamed it on lazy writers with little interest (or ability?) in continuity.
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Well, I freely blame the writers for most continuity issues! But this time, I felt as if Rory was giving Jess a very edited version of her relationship with Dean, and making it seem stronger than it really was.
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