Self-esteem is linked to high-risk behaviors in other populations but has not been examined in women aged 50 and older. This study explored how self-esteem is related to variables that can influence high-risk sexual behaviors in women over 50. A multiethnic community-based sample of 572 women aged 50 and older completed an anonymous questionnaire on sexual behaviors, sociodemographic characteristics, and psychosocial measures relevant to midlife and older women. Regression analysis showed sensation-seeking, HIV stigma, sexual assertiveness, and self-silencing predicted self-esteem in women over 50 (F = 43.632, p < .001). Factors such as relational context, interpersonal power, and silencing can affect self-esteem and may be contributing to HIV risk in this group.