The growing weight being placed on self-directed retirement accounts within the United States retirement income policy framework, and the time inconsistency challenge of individuals, particularly women, tending to under-invest in retirement savings accounts motivated the current work. Using data from the United States Federal Reserve Board’s Survey of Consumer Finances, for a period spanning from 1989 to 2019, 11 cross-sections of data, the paper investigated the role of gender in United States retirement risk-taking investment strategies of single (never married) individuals. The analysis documented increasing trends in the risk-taking of both single women and single men but recorded differences in the risk-taking profiles of the two groups, with single men taking more risk than single women in their retirement wealth building in most cross-sections, with the gender risk-taking gap dropping, nonetheless, algebraically in magnitude from 1989 to 2019.