Who can finally get Rory thinking she made a big mistake dropping out of Yale? If you guess Jess, you're right. Her old flame returns with exciting news about his life … and some blunt advice about hers.
JESS RETURNS WITH A SURPRISE FOR RORY – Rory (Alexis Bledel) is pleasantly surprised when her old flame Jess (guest star Milo Ventimiglia) appears at her grandparents' house and reveals an amazing development in his life. Rory agrees to go to dinner with Jess, and when Logan (Matt Czuchry) unexpectedly joins them, an ugly confrontation develops, leaving both Rory and Logan to face the choices they have made.
Emily (Kelly Bishop) is concerned about Rory's sudden evasiveness and tries to exert some parental discipline. Meanwhile, Luke (Scott Patterson) agrees to sponsor a local girls' soccer team and Lorelai (Lauren Graham) channels all her concerns about Rory into caring for her dog, Paul Anka.
- Lauren Graham as Lorelai Gilmore
- Alexis Bledel as Rory Gilmore
- Scott Patterson as Luke Danes
- Keiko Agena as Lane Kim
- Matt Czuchry as Logan Huntzberger
- and Kelly Bishop as Emily Gilmore
Special Guest Star
- Sally Struthers as Babette Dell
- Alan Loayza as Colin McCrae
- Tanc Sade as Finn
- Riki Lindhome as Juliet
- Elisabeth Abbott as Rosemary
- Lucy Butler as Maggie
- Kyle Chavarria as Megan
- Lexi Ainsworth as Tillie
- Channing Nichols as Bonnie
- First appearance of Jess since Season 4. The character makes his last appearance on the original run later in the season, but returns for Season 8.
- Jess wrote a book entitled The Subsect.
- Logan is threatened by Jess and Rory's past.
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- Lorelai – You've got the Queer Eye, my friend.
- Rory – It's one thing to be forced to live in the big house, but now the big house is feeling Tom Thumb tiny. My grandmother is everywhere. I'm positive there's at least five of her wandering the property like she's a Cylon.
- Luke – I want my girls to look good.
- Lorelai – Listen to Daddy Warbucks.
- Lorelai – They could make a movie about this someday … and you know who would play you? Tobey Maguire.
- Luke – He's way younger than me.
- Lorelai – But his career is hot. Go with Tobey.
- Luke – What about that Vito Morgenstern?
- Lorelai – Sure. Or Viggo Mortensen. Or Donald Sutherland.
- Lorelai – Who is their coach, Sam Peckinpah?
- Logan – So, were you two high school sweethearts? Rock around the clock, two straws in the milkshake?
- Logan – So what are we talking here? Short novel, Kafka length, or longer? Dos Passos, Tolstoy, or longer? Robert Musil? Proust?
- Logan – I was just challenging him, jeez. Hey, if Hemingway could take it, so can he.