Fan Theories Wiki
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There are lots of theories about the June 19 in Don't Hug Me I'm scared, but I think that this one is the theory behind June 19, or at least a freaky coincidence. The date everyone has been raving about is June 19. But on that same day in the 1800s, all American slaves were freed. This could symbolize how the main characters of Don't Hug Me I'm Scared are a slave to the media, and, one by one, they are being broken off, or freed.

In Don't Hug Me I'm Scared 5, Reggie, the Bird, keeps getting phone calls from a red telephone, symbolizing the red puppet that "Died" in the last episode (He became consciously aware of the outside world and was released Into reality). And every time Reggie picks up the phone, he wakes up in an operating room that symbolizes reality. And once Reggie is finally free, the media tries to "punish" him, and pretty harshly too. This symbolizes how the media is forcing you information, some that isn't true, and eating the viewers to become slaves to the media, so it can live on. Notice how every time Reggie tries to show that something is wrong, The puppets push him away from it, like they are trying to keep Reggie in the media to keep feeding the monster that the media is. I could go on for hours like this, but my main concern was with the juneteenth coincidence. There is one more thing that might be irrelevant, but it seems to me like the reason why everything is june nineteenth is that it was a random date chosen and this whole series goes through the course of one day. DHMIS 1 is like breakfast (They are in the kitchen), 2 is like morning tv in the living room, 3 they go out to lunch at the park, 4, they are having afternoon leisure time in their living room, and 5 they are having dinner. I do not know if this is the correct reason, but I think it is very plausible.

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