LOGAN PROPOSES ON THE DAY RORY GRADUATES FROM YALE – On the eve of Rory's (Alexis Bledel) graduation, Emily (Kelly Bishop) and Richard (Edward Herrmann) throw her a party and perform a song in her honor. At the party, Lorelai (Lauren Graham) and Christopher (David Sutcliffe) are reunited for the first time since their separation, and both are relieved to find they can still be friends. Logan (Matt Czuchry) surprises everyone at the party by proposing to Rory, but she is too shocked to give him an answer and begs Lorelai to help her decide what to do. On graduation day, Rory and Paris (Liza Weil) receive their diplomas, and Rory finally gives Logan her answer. Meanwhile; Lorelai is embarrassed about her karaoke serenade to Luke (Scott Patterson) the night before, and Luke is hurt when he overhears her saying it did not mean anything.
It is Rory's graduation from Yale and Lorelai and Sookie are busily engaged in preparation. Paris and Doyle are packing for a trip to India and Rory becomes sentimental. Lorelai nervously awaits for Logan to propose to Rory. Luke comes to Liz to choose a present for Rory's graduation and they discuss Lorelai's "serenade" from the night before. Lorelai comes to the diner and tries to understand her feelings toward Luke, but he ignores her.
At the diner, Lorelai learns that all of Stars Hollow wants to come to the graduation, but Rory has just four invitations—so at the town meeting they all decide to stage a re-enactment of the ceremony at the town square. Kirk's latest stunt involves him being suspended in a box above the Stars Hollow town square without food or water. Rory's grandparents have a party for her and sing her a special song. Logan proposes to a flustered Rory at the party and she says she must think about it.
- Logan Huntzberger – If I could, I'd also like to say a few words about my girlfriend of the last 3 years. You amaze me, Rory Gilmore. Everyday, everything that you do, everything that you are. This past year I learned that I don't know a whole lot more than I thought I knew, if that makes sense. I'm sorry, I'm a little bit nervous and I didn't think I would be. What I'm trying to say is, I don't know a lot. But I know that I love you, and I want to be with you.
- Lorelai – Well, 60-year-olds are notoriously needy. At least we'll be in sync by then.
- Final appearance of Christopher, Paris and Logan.
- In one part of the episode Richard comments on Bill Clinton's voice and how he should narrate books on tapes, the actor who plays Richard is a well-known narrator of books on tape.
- "Kirk in a box", references David Blaine's performance "Above the Below" where the illusionist was inside a see-through case suspended above the River Thames for 44 days.
- "I Will Always Love You" by Dolly Parton/Whitney Houston
- The Unbearable Lightness of Being by Milan Kundera.
- This episode's title is said by Paris before graduation and it is originally from Shakespeare's "Henry V".
- Kirk – I will be suspended 20 feet above the street in a clear Lucite box with no food or water.
- Lorelai – Like David Blaine.
- Emily – Apparently Lorelai has decided to invoke the "Don't Ask, Don't Tell" rule.
- Lorelai – Oh mom.
- Richard – Bill Clinton – that’s a speaker I would have enjoyed. I can't stand his politics, but he has a commanding presence and a nice voice. I wonder if he records books on tape.
- Richard – All right, everyone. Say "Fromage".
- Lorelai – Dad.
- Emily – Must you always do that?
- Lorelai – Entertain them with that in the Great War?