In studying naturalistic human decision-making, it is important to understand how emotional states shape decision-making processes and outcomes. Emotion regulation techniques can improve the quality of decisions, but there are several challenges to evaluating these techniques in a controlled research context. Determining the effectiveness of emotion regulation techniques requires methodology that can: 1) reliably elicit desired emotions in decision-makers; 2) include decision tasks with response measures that are sensitive to emotional loading; and 3) support repeated exposures/trials with relatively-consistent emotional loading and response sensitivity. The current study investigates one common method, the Balloon Analog Risk Task (BART), for its consistency and reliability in measuring the risk-propensity of decision-makers, and specifically how the method’s effectiveness might change over the course of repeated exposures. With the PANASX subjective assessment serving for comparison, results suggest the BART assessment method, when applied over repeated exposures, is reduced in its sensitivity to emotional stimuli and exhibits decision task-related learning effects which influence the observed trends in response data in complex ways. This work is valuable for researchers in decision-making and to guide design for humans with consideration for their affective states.