* 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. She even commented during her second pregnancy that she was an binge drinker before realizing she was pregnant with him. 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.
** Factor in his HilariouslyAbusiveChildhood and probably crappy experiences with strange guys trying make nice with him so they could get close to Liz, Jess has a lot of reason to be suspicious of this cheerful woman he doesn't know singing the praises of an uncle he barely knows.
* 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?]]
* In the revival, Emily's new life [[spoiler:volunteering at a whaling museum in Nantucket]] makes a ton of sense when you remember that when she attended Smith College for her MrsDegree, she majored in history and was involved with the DAR, an organization in real life dedicated to women in history. She likely has had a lifelong interest in history, but put it on the side when she got married. Now that [[spoiler:she's a widow and no longer involved in the DAR]], she now has some room to explore her own interests.
* The development of Rory [[TookALevelInJerkass Taking A Level In Jerkass]] makes more sense when you remember that Lorelai raised her like her friend and not her daughter, and with growing up in Stars Hollow, she's been spoiled by ''everyone''. She's never been really told "No" or disciplined in her entire life as well as being told that she's special and gifted and given everything she's ever wanted. When she tries to strike out on her own in college, that's when she encounters the realities of being told "No" and what consequences are. But because she's never really been equipped or taught how to handle setbacks, she starts lashing out and regressing to the safety of when everything did go smoothly for her.
* Rory spent her entire childhood pursuing the goal of getting into Harvard, and most of her college years with the goal of graduating Yale, but after that she had a rather vague "be like Christiane Ammanpour, travel and write and stuff" sort of "goal". This could easily be why she hasn't made anything of her life and career yet.
* 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.
* Rory is actually an attention junkie. In the revival I first thought that Paul was really pointless, didn't really bring anything to the plot, and it seemed very out of character for Rory to treat someone like that, but then you realise that growing up she was always perfect and adored and had a lot of attention on her. Then at Yale she blended in a lot more, because everyone is exceptional, and that's when she first started unraveling. So maybe Paul wasn't out of character, she's just used to having people's undivided attention and being admired, but in the real adult world that's a lot bigger than Stars Hollow it didn't just happen to her as naturally as it did in high school and living in a small town. So she used him for an ego boost when her life didn't quite pan out as it was supposed to - her career is at a standstill, even a website she thought was below her didn't want her when she got desperate, and Logan is engaged to someone else and no longer exclusively pining for her.
** She probably was extra sad about Logan because she at that point [[spoiler:knew she was pregnant]].
* The last final words as seen in the revival are [[spoiler:about Rory being pregnant]]. These are the words that Amy Sherman-Palladino really intended to end the show and if Amy really ended it on season 7, [[spoiler:Rory would be pregnant at 22 just as she graduated from Yale. It's not as worse as Lorelai getting pregnant at 16 but being pregnant just after graduating from college is just sad and terrible considering that Rory is getting ready to build her career and get a job only that it would stop because of that. Also, she's unprepared for being a mother at a very young age. Never mind on who the father is (it would still be Logan who is the next Christopher), how can Rory support her child if she doesn't have a stable job and income? Yeah, she might get support from her mom and grandparents. But she's an adult where she needs to be self-sufficient and responsible and at her age, she had to make her place in society. The final words in the revival makes sense since at 32, Rory is prepared for it despite her failing journalism career, she still has some money left whatever work she had done in the TimeSkip (how else can she travel from America to London) and working at the town's newspaper and writing a book would make amends]].
** Logan's probably paying for Rory's travel to London. There's no way she could afford it if she can't even afford to buy underwear for a year.
* When Lorelai is telling Emily about her 13th birthday and Richard taking her to the movies, she says it was "the best birthday [she] ever had" which is a sad commentary on her life pre-Rorry, though does that mean that she didn't have a good birthday, say when Rory had that giant pizza made for her and none of her birthdays after Rory were good?
* After Rory loses her virginity to Dean, she assures her mother that they were "very safe", implying that they used condoms. But their encounter happened on the spur of the moment, ostensibly totally unexpected. Did she have condoms in her room? She was visiting from college and wasn't dating anyone, why would she have stocked up for the summer? The alternate explanation is that Dean had one on him, but given that Dean was married and visiting an old girlfriend, the most logical explanation is that he knew (or at least hoped for) what was going to happen. If that's the case, it wasn't a spontaneous moment of passion, he went there deliberately to cheat on his wife.
** It's possible that she was just on birth control, and figured he would have told her if he had contracted an STD. But I also wouldn't be surprised if the implication was supposed to be that he was prepared and ready.