Gilmore Girls

Season 2 Episode 7:

Like Mother, Like Daughter

Chilton's headmaster Charleston thinks Rory isn't properly socializing and when Lorelai disagrees he tells her Rory may be taking after her mom. Rory's attempt to reach out gets her involved with a sorority while Lorilais becomes a booster.
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About Gilmore Girls:

A drama centering around the relationship between a thirtysomething single mother and her teen daughter living in Stars Hollow, Connecticut.