HIV is a serious public health problem for homeless populations. Homeless men who have sex with women have received less attention in the HIV risk literature than other homeless populations. This research uses multi-level modeling to investigate the context of unprotected sex among heterosexually active homeless men in the Skid Row area of Los Angeles. Based on interviews with 305 randomly selected men who discussed 665 of their recent female sexual relationships, this project investigates the correlates of unprotected sex during the past 6 months at the partnership, individual, and social network levels. Several different measures of relationship closeness and lack of communication about HIV/condoms were associated with unprotected sex. Controlling for relationship factors, men’s negative attitudes towards condoms, mental health, and higher number of male sex partners also were associated with having unprotected sex with female partners. We discuss the implications of these findings for health interventions.