During the first wave of the pandemic, governments introduced public health measures in an attempt to slow the spread of the virus enough to “flatten the curve”. These measures required behavioral changes among ordinary individuals for the collective good of many. We explore how personality might explain who complies with social distancing measures and who defies these directives. We also examine whether providing people with information about the expected second wave of the pandemic changes their intention to comply in the future. To do so, we draw upon a unique dataset with more than 1,700 respondents. We find honest rule-followers and careful and deliberate planners exhibit greater compliance whereas those who are entitled, callous, and antagonistic are less likely to engage in social distancing. Our experimental results show that even small differences in messaging can alter the effect of personality on compliance. For those who are more fearful and anxious, being confronted with more information about the severity of the second-wave resulted in higher levels of anticipated social distancing compliance. At the same time, we find that the same messages can have the unintended consequence of reducing social compliance among people higher in Machiavellianism.