Maximizing is characterized by aspirations for the highest standards. The current study explored the relationship between maximizing and risk-taking tendencies in decisions subject to risk. We propose that people first refer to expectation (i.e., the overall utility expected from an alternative) when taking risky decisions. If expectation clearly identifies the best option, maximizing will not be correlated with risk-taking tendencies. If not, people refer to maximizing to reach a decision. Maximizing will be positively associated with risk-taking tendencies because the “upper bound” of risky options helps achieve the goal of seeking the best. Four studies showed that risk-taking tendencies increased with maximizing when the options had similar expectations (Studies 1 to 3). When expectations between options were clearly different (vs. similar), the positive relationship between maximizing and risk-taking tendencies was reduced (Study 4). These findings provide an insight into how maximizing is related to risk seeking.