The study discussed in this article investigated psychosocial, relationship, and situational factors associated with HIV risk in a sample of 152 inner-city homeless men and women. Although men at risk of AIDS often had multiple sexual partners, women reported fewer different partners but more frequent unprotected intercourse with them. Different factors were associated with HIV risk level among men and women. In men, high-risk patterns were associated with negative attitudes toward condom use, low levels of intentions to use condoms, high perceived risk of AIDS, and low perceived self-efficacy for avoiding risk. Women at high risk of HIV infection had greater life dissatisfaction; were less optimistic and held more fatalistic views about the future; held more negative condom attitudes; perceived themselves to be at risk; and frequently used alcohol, marijuana, and crack cocaine. HIV prevention efforts tailored to the different risk circumstances of men and women are urgently needed in social services programs for homeless people.