Gilmore Girls Season 5 Instead of kicking Jess out at the end of Last Week Fights, This Week Tights, Rory and Jess slept together, after which Rory told Jess she couldn't go away with him. Sleeping with Dean at the inn test run didn't happen. Lorelai and Luke did get together. Three months down the line Rory went to see Jess in New York, but after someone telling him Rory was there she waited fifteen minutes and Jess not coming to talk to her she left him a note and went back and caught a bus to Star Hollow.
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