* On at least two occasions, we see Kirk simply insert himself into a job role without permission, even when expressly forbidden. He crashes a staff meeting at the Dragonfly, and later that episode is found working in the kitchen; Sookie assumes that Lorelai hired him. When Luke chaperones April's field trip, Kirk offers to run the diner, to which Luke emphatically responds, "No." A minute later, he takes advantage of Caesar stepping out to start serving people, telling them that he runs the place. Who's to say he doesn't do this all the time? He apparently gets job after job despite being a class A moron and lunatic. What if nobody's hiring him at all? What if he's just walking in and doing job-related stuff, and they're temporarily confused about whether he's supposed to be there (i.e. someone else hired him and didn't mention it)? Then when they catch on, he's tossed out on his ear, and he does it all over again, thus explaining his long string of apparently very brief jobs.
* Jess's perpetual irritation towards Lorelai and her self-declared "Cool Mom" persona makes a little more sense by the time his mother Liz comes into town. Liz has been described by both Luke and Jess as extremely flaky and negligent in raising her son and a throwaway line at her wedding revealed she had been heavily involved with marijuana use in the past. Liz even commented during her second pregnancy that she was an binge drinker before realizing she was pregnant with Jess. In other words, Liz Danes is the completely opposite of Lorelai, so Jess sees Lorelai as a mere pretender and faking her "craziness" when his own mother had been wild and crazy, with the implication that he had a rough upbringing.
** Not only that, bear in mind that Jess was basically rejected by his parents because they didn't want to raise him while Lorelai rejected her parents in a fit of teen rebellion. Her attempt to parlay this into relating with him comes off as condescendingly patronizing in hindsight. It would have further exacerbate his irritation at being shipped off to Stars Hollow against his will.
* It seems odd that Rory would have surpassed Paris in grades to become valedictorian at Chilton after her rough start, until you consider that it's the kind of place where a 4.0 GPA is probably borderline unattainable. Under those conditions, Rory could have outperformed Paris by a small but consistent degree over two and a half years, edging her out of the top spot. Paris' meltdown when she didn't get into Harvard probably impacted her GPA as well.
** Also, remember that when Paris started properly dating Jamie during their last year, she had a bit of difficulty with concentration in class for a while.
* Why does Rory want to be a Foreign Correspondent? She's grown up in a small town with the same people and loves books. She probably was excited to have some adventure and write instead of just read about adventures.
* In the first season, Emily Gilmore is totally supportive and even encourages Lorelai to date Luke. However, she later tries to break them up when they actually get together in Season 6. While this is may just be a continuity error, it actually makes sense. In season one Emily and Lorelai just started being a part of each others lives again and Emily probably wanted back in Lorelai's good graces a bit more by showing she's okay with this. Also, Lorelai wasn't interested in Luke, and it's a lot easier to be supportive of something that is a minute possibility, and Emily barely knows Luke anyway. Most importantly, Emily always wanted Lorelai to end up with Christopher. In the first season, this was barely a possibility as Christopher had been out of the Gilmores lives for ages, but by the Sixth season he'd been around and he and Lorelai had attempted a relationship multiple times, so Emily believed they had a chance and pushed Lorelai the direction she wanted.
* In season five, when Rory is researching the Life and Death Brigade it seemed a little weird that she didn't ask her grandfather about it. After all, he's a Yale legacy and has connections all over campus. But later on, when the Huntzburgers are displeased with Logan and Rory dating, it makes sense that Richard was not part of the Life and Death Brigade and that is the difference between the two families that makes the Huntzburgers think they are better than the Gilmores.
* In "Rory's Dance", Rory and Dean leave a Chilton party early, and then spend time walking around Stars Hollow before they accidentally fall asleep in Miss Patty's studio. When Rory returns home the next morning, an angry Emily believes Rory and Dean slept together on Patty's yoga mats. Fast forward to "Say Goodbye to Daisy Miller", and [[spoiler: guess where they have sex for the second time?]]

[[AC:Fridge Sadness]]
* Rory and Jess' final interaction in season 6 has a bit of an abrupt ending, showing that the two still have great chemistry but at the time, Rory is still in love with Logan and leaves with Jess looking sadly after her. Seems like a depressing way to end things for them, (specially with all the CharacterDevelopment Jess has gone through), until you learn that WordOfGod apparently meant for them to end up back together had the show run an 8th season. Jess was even supposed to appear in season 7, but then Amy quit as director thanks to ExecutiveMeddling and Jess' actor, Milo Ventimiglia, wasn't interested in working for another director. It would explain why that final interaction between him and Rory was left without closure.