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Lorelai and Rory each reach a turning point in their love lives: Rory seeks reconciliation with Dean, and Lorelai must decide her future with Max.

Rory’s pain over her breakup from Dean leads her to lash out at those close to her. Lorelai begins to worry that she has passed her intimacy issues on to her daughter.

Rory gives Emily a walking tour of Stars Hollow. Emily becomes upset when she sees the conditions in which Lorelai lived after running away from Hartford with baby Rory.

Richard’s imperious mother comes to town and suggests Rory get early access to her trust fund. Lorelai and Emily worry how the money might disrupt the family dynamic.

Rory keeps busy, refusing to indulge in self-pity following her breakup from Dean, while Lorelai tries to convince her to give in to the grieving process.