Gilmore Girls

Season 2 Episode 14:

It Should've Been Lorelai

Christopher and his girlfriend Sherry visit Stars Hollow leading Sherry to push for a Friday night out alone with Rory to bond. So Lorelai takes Christopher to a tumultuous Friday night dinner at her parents. Lorelai, thinking she missed out on a life with Christopher, confesses her self-realization.
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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.