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We live in a pretty cool age, where we can explore the world from the comfort of our couches and computer chairs. We can watch documentaries, check out friends' photos on Instagram and Tumblr, and maybe even read a book every once in a while. In Room, Jack has a TV. He gets to watch Dora the Explorer (hey, that has "explore" right in the title) and SpongeBob, as well as talk shows, nature programs, and more. But he doesn't get to explore the world for realsies – the poor kid doesn't even know there is a real world beyond Room until he's five and he and Ma escape. Once he's in the Outside, Jack isn't just exploring the world for the first time; he's experiencing it for the first time.
Because Ma protects Jack so much while inside Room (see "Fear"), he's afraid to explore new things once outside Room.
Getting hurt (bee stings, sunburns) is good for Jack, because it lets him experience things and realize that he has the strength to push himself even more.