* {{Blooper}}: In a season 6 episode, [[spoiler:Rory tells Logan that she lost her virginity to him, when the one she lost it to was Dean.]] Of course, it's not impossible that she lied to make him believe he was her first, but she doesn't seem like the type who would.
* DawsonCasting:
** At the time of filming the pilot, Alexis Bledel (19), Keiko Agena (27), Liza Weil (23) and Jared Padalecki (18) were all extremely convincing as sophomores in high school.
** Milo Ventimiglia was 24 when he joined the show as 17-year-old Jess.
* ExecutiveMeddling:
** Heavily in season six, and once Amy was out the door, very apparent in season seven as the show was used basically by the CW in order to trap viewers into sampling the other awful wares of their inaugural season without regards to six seasons of well-established continuity or writing by such luminaries such as Jane Espenson.
** The new executive producer who came on had some odd baggage, having been slapped with a restraining order by Heidi Klum (his co-worker when he wrote on ''SpinCity'') after he wrote a bizarre and offensive one man play performed in New York about how he'd [[StalkerWithACrush really, really, really like to sleep with her]], after which he was involuntarily committed for a spell by his father. Thankfully he left the Girls alone...physically. Characteristically however...
** Dean coming back and having his affair with Rory, pretty much so that the network could remind their audience that Creator/JaredPadalecki still was there and ready for ''Series/{{Supernatural}}'', coming to the WB Thursdays next fall!
** Hal Douglas, the voice of the WB, didn't move over to the CW, thus the show lost their authoritative FatherFigure promo voice, replaced with an unknown voiceover artist who you saw more describing the wacky hi-jinks of the earlier double-shot of ''{{Everybody Loves Raymond}}'' (tonight at 6:30 on [=CW67!=]) than working as the Danny Dark of the fifth network. It also sadly proved that the brain trust at {{UPN}} rather than the WB was in charge and didn't know what to do with a successful series.
** {{Nickelback}} playing in the season seven promo teasing the infamous 'Wedding in Paris' episode. Nickelback is a band that would never go near Lane or Rory's CD players, and Top 40 music was only mentioned in derision or as a necessary evil in the background of dance scenes during the AS-P era.
** The cast photos for season seven playing up Lorelai, Rory, Luke and Logan wearing way too much spray tan at the expense of the rest of the entire cast, which didn't get one picture. Again, UPN thinking (as earlier cast photo shoots involved all of the stars and sane photographers).
** The continued employment of David Sutcliffe, who only came back in the later seasons after failing as the lead guy in ''I'm with Her'', an ABC sitcom with Teri Polo which happened to be scheduled against ''Gilmore Girls'' and was beaten in the ratings by it a few times.
* FakeNationality: Lane Kim, Rory's Korean best friend, is played by a Polynesian actress. Lane's mother, Mrs. Kim, is also played by a Japanese-American actress.
* HeyItsThatGuy:
** [[Series/BuffyTheVampireSlayer Jonathan Levinson]] is the editor for the Yale Daily News, becomes Paris's boyfriend, and is later an Emmy winner for adapting the book ''Literature/GameChange'' into an HBO film.
** Those who haven't seen the show are likeliest to recognize Lorelai as [[{{Parenthood}} Sarah Braverman]], Sookie as [[{{Bridesmaids}} Megan]] and [[MikeAndMolly Molly]], Rory as [[MadMen Pete Campbell's lover]] and Paris as [[{{Scandal}} Amanda Tanner]].
** Rory's three ex-boyfriends are [[Series/{{Supernatural}} Sam Winchester]], [[Series/{{Heroes}} Peter Petrelli]], and [[TheGoodWife Cary Agos]]. [[OneTreeHill Lucas Scott]] expressed some interest in her before he got sent off to military school.
** And her grandmother once set her up with [[Series/{{VeronicaMars}} Duncan Kane]].
** Lane didn't do quite as well - she only dated [[TheOC Seth Cohen]] and [[TrueBlood Terry]].
** [[AustinPowers Basil Exposition]] is one of the professors at Yale, who had Paris as his last love ([[DeathBySex but his death was not caused by sex]], as she will remind you quite vocally).
** The girl Jess dated before Rory would go on to make it to the end of ''Survivor'' : Gabon (and make more disastrous choices in men).
** Emily got some flattering attention from BarneyMiller when she went to a spa; Lorelai made sure to tease her about it the rest of the night.
** Emily is [[DirtyDancing Baby's mother]] and was also in the original production of AChorusLine.
** Lorelai went to a Bowie concert with [[MadMen Don Draper]]. Making it very weird that Rory later had an affair with [[MadMen Pete Campbell]].
** Lorelai also briefly dated [[Literature/{{Twilight}} Bella Swan's dad]], who she had previously known as her boyfriend in the indie rock film ''Dill Scallion'' where he played the title role.
** The {{Superman}} of ''Film/SupermanReturns'' hit on Rory and the Chilton Three at a Bangles concert.
** [[{{Glee}} Sue Sylvester]] gets verbally belittled by Emily in an early episode. Yes, you read that right.
** [[{{Glee}} Brad]] played the piano at Rory's college graduation party hosted by her grandparents.
** Francine knows how to push the buttons of Paris and Rory, which is appropriate as she was the [[Film/TheRageCarrie2 second Carrie]] (though with much less blood and gore).
** [[Series/SwitchedAtBirth Bay Kennish]] apparently had some prior experience finding her real father.
** [[Series/TwentyFour Chloe O'Brian]] appeared twice: first in a film by Kirk, and later as a potential replacement for the Stars Hollow troubadour.
** Before he went to Greendale, [[Series/{{Community}} Abed]] worked in the background of the Yale Daily News.
** Lucy went on to [[Series/BreakingBad date a New Mexico meth cooker]] before becoming [[DontTrustTheBinApartment23 the bitch in Apartment 23.]]
** Christopher's mother, Rory's grandmother, is [[Series/{{Heroes}} Angela Petrelli]]. One of her boyfriends is Peter Petrelli. Ewww.
** [[AllMyChildren Josh Madden]]/[[RizzoliAndIsles Tommy Rizzoli]] tried to hook up with Rory on Spring Break, but ruined his shot when he was too happy to see Paris kiss Rory in a club to "truly experience spring break".
** Michel's mother was played by the [[TheOtherDarrin first]] [[TheFreshPrinceOfBelAir Aunt Vivian]].
** ''ParksAndRecreation'' fans should recognize Nick Offerman (Ron Swanson) as Jackson's brother Beau in a handful of episodes.
** [[VictoriaJustice Tori]] [[Series/{{Victorious}} Vega]] attended a [[Literature/{{Thelordoftherings}} Lord of the Rings]] party catered by Lorelai and Sookie.
** Richard made something of a career playing UsefulNotes/FranklinDRoosevelt in several films (including the 1982 version of ''Annie''.
** Gil used to be in SkidRow!
** [[DesperateHousewives Mary Alice]] got a crush on Luke in a season 2 episode, and later it turns out he likes to visit a restaurant driven by Karen Mccluskey.
* HeyItsThatVoice: Kathleen Wilhoite, who plays Jess's mother Liz, is also the voice of ''WesternAnimation/PepperAnn''.
* RomanceOnTheSet: Milo Ventimiglia (Jess) and Alexis Bledel (Rory). They met when he was cast as Jess and remained together until separating in 2006. It lends quite a bit of RealitySubtext to Rory and Jess's final scenes together.
* RealLifeRelative: TJ's brother is played by Michael [=DeLuise=]'s real life brother David.
* TheOtherDarrin:
** Mia, the owner of the Independence Inn and Lorelai and Rory's surrogate mother/grandmother was played by a different actress in season 7.
** Cesar, one of the servers at Luke's Diner was played by a thin, tall Latino actor in the first two seasons, but was only really ever in the background and never had any lines. In the later seasons, Cesar was played by Aris Alvarado, who was chubby and didn't really look anything like the first, but he became one of the town's quirky characters and had the rare scene every once in a while. Viewers could be forgiven for not noticing the change.
* ScrewedByTheNetwork: Might as well be renamed Screwed by Dawn Ostroff. The WB let Amy do whatever she wanted for six seasons, but once somehow Dawn became the leader of the new CW instead of any one of the WB's competent executives, the show started its stunning death spiral towards the last half of the sixth season, and her meddling with the show to use it as part of a {{Bait And Switch}} strategy to make viewers forget completely about the well-loved WB and forget UPN ever existed alienated most of the fanbase outside of the Rory/Logan shippers. And even that small win was destroyed with the abrupt series finale where they were broken up. Both Liza Weil and Kelly Bishop (who both rarely speak ill of anyone or anything in their careers) expressed disgust publicly that a proper series finale wasn't filmed as a Plan B in case of cancellation.
* WhatCouldHaveBeen: Sookie was played by Alex Borstein in the unaired pilot, but she couldn't dedicate her time to the series proper because of her commitments to ''Series/{{MADtv}}''.
** Jess was supposed to appear in the final season, but Milo Ventimiglia refused when Amy wasn't the director anymore.

!!Misc Trivia
* Emily Gilmore's jewelry is actually Kelly Bishop's own jewelry as she is allergic to the nickel plating used on costume jewelry.
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