HIV-related stigma has been identified as a barrier to HIV testing and prevention efforts internationally and nationally. Although the prevalence of HIV/AIDS is rapidly increasing in women aged 50 and older, little is known about the HIV-stigmatizing behaviors in this underserved population. In this exploratory analysis we investigated the influence of self esteem, sensation seeking, self silencing, and sexual assertiveness on the HIV-stigmatizing behaviors in 572 women aged 50 to 93. The variables considered in this analysis included subscales for the variables self silencing (Externalized Self Perception, Care as Self Sacrifice, Silencing the Self, Divided Self) and sexual assertiveness (Information Communication, Initiation, Refusal). Contributing predictive variables in the final model included: Self esteem (beta = -.190, t = -4.487, p = .000), Care as Self-Sacrifice (beta = .125, t = 2.714, p = .007), and Silencing the Self (beta = .164, t = 3.290, p = .001). Initiation (beta = .108, t = -2.619, p = .009) and Refusal (beta = -.091, t = -2.154, p = .032). Implications for social work and health perception regarding HIV prevention in midlife and older women are considered. Development of age- and gender-appropriate strategies assisting women in addressing HIV-stigma and related influences are addressed.