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Gilmore Girls - Season 2
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Gilmore Girls - Season 2 Episode 14: It Should've Been Lorelai

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In this season, Gilmores found themselves in the midst of perfect, giddy relationships, or so they thought. Lorelai ponders a surprise marriage proposal and Rory enters her next year at the exclusive Chilton Academy and continues her on again/off again romance with Dean.
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