Sexual selection theory predicts that males, especially in their prime reproductive years, are more risk-prone than females. Risk-taking is a means to convey mate quality or “good genes” to members of the opposite sex or competitive ability to members of the same sex. Therefore, risk-taking should be more common in the presence of potential mates (intersexual selection or female choice) or in the presence of male competitors (intrasexual selection or male–male competition). Risk-taking can also be situated within a life history/ecological perspective, according to which environmental unpredictability promotes more present-oriented and risky behavioral strategies. Therefore, people living in areas of low socioeconomic status are predicted to be more risk-prone. We conducted an observational study on risk-taking in two everyday situations: crossing the road and riding a bicycle. A total of 1,030 participants, 906 road-crossers and 124 cyclists, were recorded at various intersections throughout Perth, Western Australia. In line with predictions from sexual selection, males were more likely to cross a road in high-risk conditions and to ride a bicycle without wearing a helmet. These behaviors were also most common in younger adult males. Female and male onlookers had no effect on male risk-taking, which suggests that norm adherence is a more powerful force than sexual selection in shaping risk-related behaviors. Area-level socioeconomic status was strongly associated with the frequency of risk-taking, implying that environmental stressors can affect risk attitude. Elucidating the ultimate drivers behind everyday risk-taking has important practical implications for risk intervention strategies.