Season 5 Ep. 18
What Dean finally says to Luke after giving him an attitude for weeks, though I'm not sure even how he knows how Luke feels about him not being good enough for Rory, because I don't think he ever mentioned it in front of him, so I'm not really sure why Dean is giving him an attitude at all, maybe I'm forgetting something... but Dean saying he and Rory and Luke and Lorelai are the same thing, simply doesn't make any sense... because while Rory is young and went off to college, when has Lorelai ever given any indication that she's dying to get out and see the world? It just made no sense.
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