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Playfulness is a vague and ambiguous term. While it is easy to realize that a specific situation is playful, the concept itself is hard to grasp. Situations shift in and out of playfulness, leaving the term with hazy borders. This essay attempts to contribute to analysing playfulness in a rather unusual form. Instead of directly approaching the target, we take a stroll into the borderland that surrounds it, embarking on a quest to mark the borders of playfulness.