LORELAI: Ugh, Jess, let me give you a little advice. The whole ‘my parents don’t get me’ thing, I’ve been there.
JESS: You have, huh?
Lorelai follows Jess again, and for the third time finds him doing something in her house on the sly. This time, it’s taking a beer from her fridge.
Lorelai handles this awkward situation rather neatly, and it’s only after Jess balks at coming in to dinner and mocks her cosy small-town life (“Well geez, Ms. Gilmore … that sounds plum crazy”) that she starts handing out unsolicited advice. It’s (mostly) well-intentioned and she is genuinely trying to help Luke if not Jess, but it goes down very badly.
It’s hard not to have some sympathy with Jess here, because Lorelai is very patronising saying that “she’s been there”. Yes, she was a smartass, misunderstood, and misbehaving teenager like Jess, but their lives were hardly parallel.
Lorelai grew up in a wealthy, privileged household, her father didn’t leave them, her mother wasn’t unreliable and impractical. Nor did her mother give up on her and basically throw her out to live with a relative she barely knows in a small town hours away from her home. In fact, it was Lorelai who rejected her parents and ran to the sanctuary of Stars Hollow.
Lorelai has the rare experience of taking someone on who is intelligent enough to match her in wits, and confident enough to stand up to her. It obviously comes as a shock, and by the end of the argument, Jess has made a crude yet insightful attack on the possible sexual relationship between she and Luke, and Lorelai has sunk to playground levels of retaliation, showing that she hasn’t grown up much since being a teenager.
It is Lorelai who retreats inside while giving a parting shot, so it’s round one to Jess, but Lorelai gets the last word.
NOTE: Edited with the kind assistance of helpful reader Daniel A Huth, who stopped me from imagining a fridge which wasn’t there.