Lorelai is becoming seriously involved with Max (guest star Scott Cohen) just as she finds herself getting in the middle of another relationship when Luke's girlfriend Rachel (guest star Lisa Ann Hadley) accuses him of being in love with Lorelai. Meanwhile, Rory has her own romance drama and tries to work up the courage to win Dean (Jared Padalecki) back.
Having made up with everyone, Rory finds the 'Dean box' in the closet at home and tells Lorelai why they broke up in the first place. Lorelai encourages Rory to follow and risk her heart for love, and Rory tries to talk to Dean several times, but her nerve fails her. At the Town Meeting, she stands up and gives a speech in defense of the troubadours in the great 2001 Town Troubadour showdown, and Dean notices.
Luke shows up unexpectedly at Lorelai's house to fix things, at odd times, and Lorelai talks to Luke about his relationship with Rachel, who's had trouble tracking Luke down and has been asking Lorelai about him. Luke tells Lorelai that his relationship IS what he wants and thanks her for the talk. Meanwhile, Lorelai and Max continue their taken things slow, going on dates and enjoying each other's company. Lorelai even brings Max to the aforementioned Town Meeting. After the meeting Luke finds Rachel packed and ready to say goodbye. He gets angry, thinking she's leaving him again, but Rachel confesses to leaving because of Luke's feelings for Lorelai. Luke tries to deny it, but falters and Rachel encourages him to open his heart to Lorelai, and leaves for good.
At Chilton, Tristan persistantly asks Rory out, who is not interested and, in the process, ruins Rory's friendship with Paris when he tells the Mean Girl Trifecta that he and Rory are going out. Rory heads home to find Dean waiting outside Chilton, but Tristan follows and Dean turns to leave before Rory tells him to stay because she loves him. After an implicit face-off between Luke and Max, the latter tells Lorelai they should marry, and Lorelai takes offense to it being a way to end their fight. The next day, she walks in to the Independence Inn to find 1000 yellow daisies have been delivered – one of her aside depicts during her fight with Max of what a real proposal should be. She calls him and he gives a beautiful speech, declaring his intention to marry Lorelai. The season ends with the Gilmore Girls running toward each other, euphorically in love.
- The Town Troubadour is elected the sole troubadour of Stars Hollow, but he makes amends with the other troubadour, who shows up later in the year, selling vegetables, and years later again, playing music in the town square.
- This episode marks the last time Rachel appears.
- Tristan finally asks Rory out straight up – but she turns him down.
- Rory falls out with Louise, Madeline and Paris yet again.
- After Rory finds the Dean-box and talks with Lorelai, a boom mic is visible at the top of the frame.
- honey don't think | GRANT LEE PHILLIPS
- sadness soot | GRANT LEE PHILLIPS
- one line | PJ HARVEY
- Rory and Dean reunite
- everybody needs a little sanctuary | GRANT LEE PHILLIPS
- how to dream | SAM PHILLIPS
- my little corner of the world | YO LA TENGO
- swan lake op. 20a: sea in the moonlight | TCHAIKOVSKY
- Lorelai – The fricking Blue Man Group is outside our house!
- Rory – No, my insane mother Margot Kidder Gilmore woke me up!!
- Lorelai – I had the weirdest dream. We were in our house but it wasn't our house. It was a Kentucky Fried Chicken.
- Lane – I miss the old Rory.
- Rory – I miss the old me too.
- Lane – And I feel bad for the new Rory.
- Rory – Well, she's staging a comeback.
- Lane – May it be more successful than Peter Frampton's.
- Rory – You swear? On the life of the lead singer of Blur?
- Lane – On the soul of Nico, I have not seen Dean with another girl.
- Tristan – You're into PJ Harvey, right?
- Rory – Yeah, how'd you know?
- Madeline – Ok, so now I've decided that I'm completely into Judy Garland. Did you see the TV movie? Pretty intense.
- Louise – I think it features my mother's medicine cabinet in that.
- Madeline – (referring to Judy Garland) She was the Courtney Love of her day.
- 2nd Troubador – I run a Kinko's in Graten.
- Lorelai – And that starts with ceasing work on the Winchester Mystery House here.
- Rory – Mary? Oh no, not the Virgin Mary thing again.
- Louise – Not virgin, Typhoid.
- Kirk – I don't question the orders. I merely follow them.
- Michel – A job well done, Mr. Adolf Eichmann.
- Lane – "You're cheerleader material"--cheerleader material! Just like that I couldn't believe that I almost went full Matrix on her.