It's from Season 3, Episode 2 "Haunted Leg".
If you're a Gilmore Girls virgin, first of all- shame on you. Second of all, context- Christopher is Lorelai's high school boyfriend and Rory's father, but he was never really around after Rory was born.
In season 2, Christopher finally gets himself together when he gets with this woman Sherry. At the end of the season, they break up and he and Lorelai get together. And then Sherry tells Christopher that she's pregnant, and he goes back to her, determined to be the good father that he never was to Rory.
Lorelai breaks off all contact with Chris after that, and eventually, he shows up at her parent's house where Lorelai and Rory have dinner every Friday night.
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