By contrasting normative (how we should decide) and descriptive (how we actually decide) approaches, this chapter examines the complexity of decision-making. In order to logically establish decision context, which can be crucial in a legal context, game theory and the prisoner dilemma are first described. After that, a basic example is presented and solved using several approaches, beginning with the explanation of a basic schema to approach choice problems. Uncertain, univalent, polyvalent, and certain dilemmas are described along with helpful solutions for each potential conundrum. After that, descriptive models are presented, with an emphasis on the heuristics and biases approach and the bounded rational model. Several biases and heuristics are discussed along with real-world instances and uses. Prospect Theory is then introduced as an alternative way to formally look at decision problems, including both empirical and theoretical considerations. Within the chapter the notion of emotion is taken up again, since they can strictly influence decision-making even in professional situations. Along with the risk as emotion hypothesis, the affect heuristic is utilized as an emblem of this influence. Lastly, the dual thinking model is described, which includes System 1 (quick, automatic, intuitive, emotive, and heuristic-based) and System 2 (slow, deliberative, analytical, logical, and resource-demanding). Both systems must be used in balance while making decisions. Heuristics are not merely shortcomings indeed. They are practical instruments that frequently work well in a complicated environment with little data. However, also deliberated decisions are important to improve professional effectiveness and prevent errors. Being mindful of the possible drawbacks of intuition, a tacit knowledge refined by experience, is essential to developing professional skills.