As the relationship with Rory's (Alexis Bledel) teacher Max (guest star Scott Cohen) grows more serious, Lorelai (Lauren Graham) panics and decides to end it, but her attempt to break up with him during Parent-Teacher night at Chilton causes even more trouble at school for Rory.
Lorelai and Max have an incredible dinner date, replete with banter, good eats and... Proust. Rory 'reprimands' Lorelai for coming home late, stating that her mother looks happy, which Lorelai confirms that she is. Paris Geller is suffering the gossip mill as her parents go through a publicised divorce, Madeline and Louise not shying away from joining in. Rory and Lorelai plan on going ice skating, and Rory, who is warming to the idea of Lorelai and Max, asks if they should invite Max along.
Lorelai freaks out and discusses her fears with Sookie and, inadvertently, offends Sookie's own romantic life. After making amends, Lorelai's words prompt Sookie to ask out Jackson. Rory gets caught in the middle of Lorelai's attempt to end things with Max, which culminates in a steaming kiss on Parents Day at Chilton. Paris sees them and spreads the news, humiliating Rory, Lorelai and Mr. Medina. Rory later gives out to Paris for sharing the personal details of the teacher Paris allegedly likes and Rory offers Paris friendship to help cope with her mess at home.
Meanwhile; Lorelai apologises to Max for trying to break up with him, reversing her position and opening up to the man she told her mother could be the one. Max, however, is overwhelmed by his own actions and their passion and decides to cool things with Lorelai.
- Max breaks up with Lorelai.
- Lorelai says that Sookie has not been in a relationship in years.
- Sookie asks Jackson out.
- Emily berates Lorelai for her actions, before realising too late that her daughter is heartbroken over possibly losing Max.
- According to Lorelai, she and Rory once had a Damienesque hamster, Skippy.
- In the scene when Max quotes Emily Dickinson in class, you see the boom operator (at first in the window, then on top of the screen).
- In Search of Lost Time by Marcel Proust
- Swann's Way by Marcel Proust (Max loans it to Lorelai)
- Michael Crichton
- Also referenced: Dante, Shakespeare, Homer, Emily Dickinson, Walt Whitman
- Louise – Dumb girls crave smart men. It's the whole Marilyn Monroe-Arthur Miller syndrome.
- Lorelai – If I hadn't stopped watching This Old House I'd be 500 pounds right now.
- Lorelai – Rory and I have a skating date.
- Rory – I'm Nancy Kerrigan.
- Lorelai – And I'm Tonya Harding. I'm going to do the whole shoelace coming untied, nervous breakdown, let me start again act and everything.
- Lorelai – Wooo, how sordid?
- Rory – Well, it's not the Rick James incident, but Hugh Grant should be feeling pretty good about himself...
- Lorelai – Like a normal hello, not like a "Here's Johnny" kind of hello?
- Lorelai – Wow, you're the new "Heather".
- Rory – Don't.
- Lorelai – Oscar ...
- Rory – Felix! (referring to The Odd Couple)
- Lorelai – Fine.
- Max – I'm the one that started the kiss.
- Lorelai – I'm the one that knocked it up to NC-17.