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1* AlternativeCharacterInterpretation: Did Hugh always plan to take Lisa away to England and never see her family again before he even met them, which would just make him an elitist snob? Or did he decide at the last minute that he couldn't stand the Simpsons anymore after the short time he spent with them, which would be a little more sympathetic?
2* HarsherInHindsight:
3** Tragically harsh: "John John John Kennedy" is listed as one of the arrested celebrities. UsefulNotes/JohnFKennedyJr ("John John") died four years after the episode was released in 1999, at the age of 38, childless.
4** The news report about the celebrities being arrested and the remark of Heather Locklear Fortensky being at large becomes this given Locklear's various legal issues since the late 2000s.
5** Both Maude Flanders and Edna Krabappel are alive and elderly in the TimeSkip. Maude dies in Season 11, Edna marries Ned Flanders in Season 23, before she herself dies in Season 25 [[TheCharacterDiedWithHim following the death of her voice actress, Marcia Wallace]].
6** Similarly, Troy [=McClure=] was shown alive and elderly, teaching the Pepsi-sponsored math class. In real life, both [=McClure=] and Creator/PhilHartman's other recurring character, Lionel Hutz, [[ActorExistenceLimbo got retired from the show after season 10 due to Hartman's death]] (though still make non-speaking cameos, so at least it avoids conflicting with this episode).
7* HilariousInHindsight:
8** Believe it or not, the line about Music/{{The Rolling Stones|Band}} having a tour in the 21st century was supposed to be a joke about how it would never happen.
9** Creator/JimCarrey being revered enough to have his own film festival, this being before the likes of ''Film/TheTrumanShow'', ''Film/ManOnTheMoon'' and ''Film/EternalSunshineOfTheSpotlessMind''. The joke also references how he suddenly managed A-list stardom with ''three'' hit movies in 1994 (''Film/AceVentura'', ''Film/TheMask'' and ''Film/DumbAndDumber'') by imagining he'd keep up that pace, especially as sequels to his early hits were on the drawing board then, but he's never had more than two releases in a calendar year since, and only occasionally made sequels to his own films.[[note]]Out of the three films mentioned, the only one which had a sequel released immediately and with Carrey onboard was ''Ace Ventura'', as he wouldn't agree on a ''Dumb and Dumber'' sequel until 20 years later, and ''The Mask'' got [[Film/SonOfTheMask a pseudo-sequel]] that didn't feature Carrey a decade later.[[/note]]
10** The soy pops in the vending machine, considering that soy products are more common now than they were in the 1990s. Likewise, the use of cards for nearly every transaction.
11** The joke about Hugh's Uncle Eldred getting medicine from the British National Health System in 2010; when in reality, the US was in the middle of a fight about healthcare reform.
12** The communicator watches were [[https://en.wikipedia.org/wiki/Apple_Watch off by about five years]]. Video phones [[https://en.wikipedia.org/wiki/FaceTime weren't]], though.
13** The CocaPepsiInc joke about "CNNBCCBS: A division of ABC" because of Fox Network now being a division of Disney (and so technically a division of ABC).
14** The joke about Fox Network becoming a hard-core porn channel: although Fox hasn't gone ''that'' far, channels such as FX and FXX have gotten a hefty amount of publicity and recognition through highly acclaimed shows (and a few others that were bombs) that cater to mature audiences.
15** During an exterior shot of London, there's a futuristic skyscraper visible in the background. 14 years after this episode, The Shard was erected as London's tallest building which fits its shape and location.
16** Bringing up the Dr. Dre Hall example again, Dre would become a major benefactor to USC, which would receive a new building, the Iovine and Young Hall.
17** Just the fact that this is a future episode with the Simpsons kids all grown up set in 2010 when, due to ComicBookTime, the main focal character of this episode, Lisa, wouldn't have even ''born'' for part of that year from season 30 onwards, and not in that year at all from season 31.[[note]]Possibly even by the very end of season 29 and 30 respectively.[[/note]]
18** Lisa being a vegetarian in her adult years, a whole season before it [[Recap/TheSimpsonsS7E5LisatheVegetarian becomes canon in the present]] (and, as far as we know, this episode did not influence that one).
19* JerkassWoobie: At first Hugh is just TheWoobie. His time with the Simpsons causes him a pretty noticeable amount of misfortune in a seemingly short amount of time. His [[DeadpanSnarker snarking]] doesn’t push him over to this trope, as it's still fairly civil, and he never acts openly rude to those around him. But his complete LackOfEmpathy over making Lisa leave her loved ones behind forever makes him this. Yes, he may have had several unpleasant interactions with them, but they still meant well and what he was planning to do would've greatly hurt both them and Lisa. This causes Lisa to leave him, which increases his [[TheWoobie woobie]] levels, as despite the breakup being the fault of his own selfishness, he's still a guy who lost the woman he genuinely loves on his wedding day.
20* MemeticMutation: The Happy Squirrel has been respected by a few actual tarot decks, and some are even arguing for its inclusion as an official addendum to the deck representing uncontrollable chaos and keeping oneself out of business that does not involve them.
21* StoicWoobie: Homer can also count here. First it's made clear that his father has passed on by the time of these future events. Then Homer tries to genuinely bond with Hugh, and in a very sweet moment, he presents him with his father's cufflinks that Abe wore at his wedding, which Homer then wore at his own, asking that Hugh continue this tradition by wearing them when he marries Lisa. Hugh promises that he will. Despite truly liking Lisa's fiancé and being excited that he'll honor his promise, on the day of the wedding, Homer discovers that Hugh has gone back on his promise, not wanting to be embarrassed by Homer's childlike gift. Despite this betrayal, Homer puts on a brave face and tries to hide his hurt feelings from Lisa so that he doesn’t spoil her wedding day. Lisa, knowing her father's emotions are wounded, goes to Hugh and convinces him to wear them. At which point he drops the act that he's not just annoyed by Homer and his family, he truly dislikes them and plans to separate Lisa from them after the wedding, which causes Lisa to leave him. We don't get to know how Homer reacts to this news, but given he really did seem to like Hugh, he always meant well in his interactions with him, and his speech to Lisa making it clear how much she means to him, it's not a stretch to assume that the usually emotional Homer loses his StoicWoobie status and will go on to blame himself for Lisa's failed marriage, even though the blame is much more on Hugh.
22* ToughActToFollow: This episode serves as one for basically every other episode to deal with possible futures for the Simpsons family, due to how believable but still interesting most of the future Simpsons are and it having a good mix of realism and heart. At least a chunk of the reason that "[[Recap/TheSimpsonsS11E17BartToTheFuture Bart to the Future]]" was so widely disliked at release was that it had to compare itself to this episode.
23* UnintentionalPeriodPiece: Odd for an episode set in the future, but the name "Heather Locklear Fortensky" puts it into this territory. At the time the episode was made, construction worker Larry Fortensky was fresh off of his divorce from Creator/ElizabethTaylor, but in no other era would he be a celebrity with a recognizable name.
24* ValuesDissonance: Lisa feeling uncomfortable wearing a [[VirginInAWhiteDress white dress]] nowadays would seem weird to modern viewers. Now most people just see wearing white as normal whether or not you've had sex before.
25* TheWoobie: Lisa definitely counts. She meets Hugh, the guy of her dreams, and everything seems to be going really well between them. But then on the day of her wedding, Hugh makes it very clear that he doesn't like her family at all and actively plans to keep her separate from them for the rest of their lives. This causes Lisa to rebel and make it clear that if she has to choose between him and her family, she'll pick the latter. They split up and Lisa never sees him again. On the bright side though, it's clear that while her first romance failed, she still has her loving family by her side, and it's implied that she'll go on to find someone better for her.

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