Lorelai (Lauren Graham) and Rory (Alexis Bledel) are thrown for a loop when Christopher (David Sutcliffe) brings his new girlfriend Sherry (guest star Madchen Amick, "Twin Peaks") to Stars Hollow and she makes it clear that building a close relationship with Rory is her top priority. Meanwhile, when Emily (Kelly Bishop) learns about Sherry, she is furious with Lorelai for blowing her last chance of getting together with Christopher.
Christopher comes to town on a business trip with his girlfriend Sherry Tinsdale 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 Friday Night Dinner, and invites Christopher along 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 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 believes she's always thought that they would get back together, too, and that's one reason 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. Lorelai immediately apologizes, saying she didn't mean it blamefully, but more as self-realization, but Christopher is too angry to listen.
- Michel – Get away from me, evil girl! Never will I do anything for you again, ever!
- Rory – Well, if it makes you feel any better you had really good form
- Michel – (disparagingly) You are your mother's child (leaves)
- Rory – (cheerfully) Thank you!
- Rory has Kirk and Michel help in a covert operation to get Lane the newest Belle & Sebastian single.
- Lane is grounded for having secretly been 'dating' Henry.
- Rory and Paris win a debate for Chilton on assisted suicide, competing against Brad Langford who has transferred to the competing Hillside Academy.
- Sookie is at the debate and meets Chris for the first time. She also meets Sherry.
- "Legal Man" by Belle and Sebastian
- Lorelai – How was it that suddenly everyone in the world was saying "music has charm to sooth the savage beast" when it was written "breast"?
- Lane – My mom's done everything but slap a Dr. Dre ankle bracelet on me.
- Lorelai – Schmitty's over the hill. He's washed up. Put him in Cooperstown.
- Rory – Not the Two Fat Ladies again.
- Rory – No two people know more about assisted suicide than the two of us. Kevorkian called today for a couple of tips.
- Paris – Let's not harbor any Pinteresque fantasies.
- Christopher – I hear you're the greatest chef after Alain Ducasse.
- Rory – Well, having company is about making sacrifices.
- Lorelai – Martha Stewart?
- Rory – I paraphrased Proust.
- Lorelai – You, me, Martin Sheen all chained to the same tree.
- Lorelai – You should get a show on the Home and Garden channel, Mom.
- Rory – Well, what did she think, that you were gonna come home and find a rabbit boiling on the stove?
- Rory – I feel like I'm on The Ricki Lake Show.
- Rory – But I also pictured you with Pee-Wee Herman. We lived in his playhouse and we'd be talking to Chairy and Captain Carl would be walking by.
- Rory – Oh, and later I pictured you marrying Matthew Broderick, and we lived in New York in this great apartment in the village and we would talk about his Ferris Bueller days.
- Lorelai – Ah yes, the Gilmore family players rival the Barrymores for their sophisticated, dramatic productions.