The present qualitative study investigated the link between human playfulness as a personality trait, views of wild animals (wolves, crows, owls, and coyotes), and connectedness to nature. The link has not been previously investigated directly. Twenty-one participants deemed to be playful were interviewed about their playfulness, connectedness to nature, and views of wild animals. The link between the three was found to be tenuous at best, and connectedness to nature was established as a key mediator of playfulness regarding views of wild animals. Although not explicitly investigated, views of relationships to one’s animal nature appeared to be an important influence on connection to nature and views of wild animals. The understanding of how playfulness connects us to our instinctual nature, to other animals, and to the natural world is likely much more complicated than originally hypothesized.