Gilmore Girls: Season 2, Episode 14

2 - 14: It Should've Been Lorelai

Christopher comes to town on a business trip with his girlfriend Sherry in tow. Since Sherry and Christopher's relationship is getting serious, Sherry wants to begin bonding with Rory -- on Friday night. Without consulting Emily, Lorelai excuses Rory from the Gilmore Friday night dinner, and takes Christopher with her instead. When Emily finds out about Sherry over cocktails, she has a meltdown and rushes off to the kitchen. Lorelai follows her there and finds out that Emily has always envisioned that Lorelai and Christopher would end up together. Now that she sees that this isn't going to happen, Emily blames Lorelai for always keeping him, and everyone else, at arms length. After mulling over her mother's words, the next morning Lorelai tells Christopher that she's always thought that they would get back together, too, and that's why she's never had a relationship that lasted, including the one with Max. Christopher gets very angry, refusing to accept the responsibility for the way Lorelai's romantic life has turned out.