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  • Alternate Character Interpretation:
    • The "George is secretly transgender" view point is a popular one as she seems to have traits that go above and beyond what you would normally expect from a tomboy. She even outright declares that she wishes she wasn't born a girl at one point, although that was arguably more to do with the Stay in the Kitchen mentality of the time than anything else.
    • Another interpretation is she is a Boomerang Bigot with a lot of internalized misogyny and self-loathing. The self-loathing part is more evident in Five Go to Mystery Moor, where the group meets a girl who is basically George with another name. They hate each other from the first moment and George looks down on her because she uses the male version of her name and dresses like a boy, the same things George does all the time!
  • Heartwarming Moments:
    • In Five on Kirrin Island Again, George travels to the island in the middle of the night, when she suspects that Timmy in danger, having been left on the island to guard her father. Her reunion with her usually irascible father is quite touching.
    • In Five fall into Adventure, Dick comforts the gipsy girl Jo when she is tearful from having been mistreated by her father, showing genuine kindness. She makes a point of liking him more than the rest of the Five for this.
  • LGBT Fanbase: George is popular with lesbians as well as trans people.
  • Tear Jerker: One particularly sad moment is in Five go off in a Caravan, when their circus friend Nobby's dog Barker eats poisoned meat, which was intended for Timmy. Barker recovers at the very end of the book.
  • Values Dissonance:
    • Julian and George's clashes. Back when the books were published Julian was a Reasonable Authority Figure dealing with an unreasonable girl, but today he comes across as bossy and chauvinistic, especially when he forces his Stay in the Kitchen mentality on her.
      George: It's stupid being a girl! Always having to be careful when boys can do as they like. I'm going to sleep in a barn anyway: I don't care what you say, Ju.
      Julian: Oh yes you do. If you go against the orders of the chief, that's me, my girl, you won't come out with us again. Like it or not, girls have to be taken care of.
      George: But I would have thought boys hate looking after their sisters and girl cousins, especially girls like me who don't like it.
      Julian: Well, decent boys like looking after their sisters and girl cousins; and oddly enough, decent girls like it. But I'm not going to count you as a girl, decent or otherwise. I'm going to count you as a boy who's got to have an eye on him - my eye, see? So take that look off your face, and don't make yourself more difficult than you already are.
      George (laughing): All right, you win. You're so jolly domineering these days I feel quite afraid of you.
    • There are many casual references to Corporal Punishment from parents or even adults not related to the child. That was normal back then, but now they sound quite abusive.
      "He's got a stick! I hope he whacks you hard."
    • The portrayal of different classes. Anyone born lower class is expected to stay there and be happy with the limitations of that time. Whenever a lower class character attempts to move up, they're inevitably treated as villainous.
    • George's extreme disdain towards being seen as a girl is supposed to be her rebelling against the strict gender roles of the period. Reading the books with a modern POV, she reads more like a young trans boy than originally intended.
      "It's stupid being a girl!" said George, for the millionth time in her life.
    • The sexist scenes. Whenever any spying is to be done by only part of the group, the boys always insist they do it. This is reasonable for Anne, who doesn't enjoy adventure and is the youngest and most timid. However, George hates to be left out. Whenever she wants to join the boys, they tell her they'd love to have her along, but that someone needs to stay and look after Anne. Nowadays, it would be reasonable for George to say "Why can't one of you look after Anne this time, so I can have a turn?" But due to the times, she never argues the point.

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