Death is a sensitive topic, and discussing death with children may be difficult for parents, especially parents who are uncomfortable with emotional expression. Many factors are associated with parents' decision to discuss death; however, a dearth of recent literature existed examining the role of parental emotional expressiveness and discussing death with children. Using Jackson's communications theory within the broader family systems theory, this exploratory non-experimental quantitative study examined if one or more of the selected variables of parents' emotional expressiveness, parents' gender, and any previous discussions about death with a child adequately predicted the age of a child when parents felt it was appropriate to discuss death with a child. Prospective participants were parents recruited from a national online university (n = 175). Multiple linear regression analysis using enter selection was conducted on the data from the instruments that included the Attitudes towards Emotional Expression Measure and the demographics questionnaire. Results indicated no significance between the predictor and criterion variables. Despite the non-significant results, this study has the opportunity to impact positive social change by encouraging further research to understand the association, if any, between emotional expressiveness and death conversations, de-stigmatizing discussions of death and bereavement, and informing parents and professionals regarding discussing death with children to help children cope with their emotions in bereavement.