Floods are one of the most lethal natural hazards. Recent studies show that in a large percentage of flood-related fatalities, victims engage in risk-taking behavior by getting deliberately in contact with floodwaters. This study integrates behavioral psychology and situational environmental factors with the aim to examine why individuals undertake such risky behavior. In particular, we draw on the theory of planned behavior (TPB) to link water depth perception with the intention of car drivers to enter floodwaters. The hypotheses on which the study was based were that the depth of the water adversely affects the driver’s intention to enter floodwaters, and that this effect is mediated by a behavior-favorable attitude, a behavior-favorable subjective norm, and perceived behavioral control. Further, to understand the conditions under which this process works, the moderating role of past behavior in the above relationships is also examined. Results from an experimental study (n = 1940) show that water depth perception affects intention. Attitude, perceived behavioral control, and normative beliefs operate as the underlying psychological mechanism that leads to the mitigation of intention in higher water depth situations. Interestingly, past risk-taking behavior is found to be a significant condition under which this process works, by mostly affecting individuals’ attitudes. Mediation and moderated mediation analyses were conducted to estimate causal relationships. The findings provide evidence of the significant interaction that environmental, psychological, and precedent behavioral factors have on behavioral intentions.