UX practitioners are encouraged to create simple designs, however user research often shows that humans are complicated and finicky. If we ignore the fact that humans are driven by complex motivations and needs, we not only fail to be true user advocates, but can also miss opportunities to innovate. How can we create designs that are simple and at the same time address complexity of human behavior? In this poster presentation we will discuss examples from user research projects conducted for a major online ticket reseller showing complexity of human behavior related to attending live events. In addition, we will suggest guidelines based on cognitive science and psychology of decision making for how to design for complicated human needs.