This research reports an investigation into whether the personality aspect of self-confidence affects the compromise effect. We hypothesize that highly self-confident people have greater certainty in making decisions and are more attracted to risk-taking, which makes them less likely to choose the safe or middle option in a large choice set. The three studies involved are conducted using between- and within-subjects experimental designs. Various product categories are used to generalize the findings. Study 1 looks at purchasing decisions and utilizes three scales of self-confidence, risk preference, and uncertainty; it demonstrates that consumers with high self-confidence are less likely to choose a compromise option due to high certainty in their decision-making. Study 2 discovers that people with low self-confidence are more likely to choose the middle option in a risky condition than in a nonrisky condition. Study 3 decomposes self-confidence into general and specific self-confidence, and reveals that people with low general self-confidence and low specific self-confidence are more likely to choose the middle option.