LORELAI: You look tired.
RORY: I just haven’t been sleeping very well lately.
LORELAI: How come?
RORY: Just have a lot on my mind.
It’s a few weeks since Rory and Dean ended their relationship, and she seemed to be coping pretty well. But perhaps that was just because she had a few distractions, such as a surprise visit from her great-grandmother, a group project to work on, spending an afternoon with her grandmother, and getting her own bedroom at her grandparents’ house.
Now that it’s back to normal life with nothing much happening, Rory is having trouble sleeping. When she sees Dean walk past the diner as she and Lorelai play a “who would you marry?” game with passers-by, Rory looks miserable.