Sex trade behavior is fairly common among homeless adults and may contribute to higher rates of HIV/AIDS in this population. This study provides a detailed examination of the sex trade-related attitudes and behaviors of homeless men by: (1) determining the prevalence of sex trade-related behaviors, including sex with female sex workers (FSWs); (2) identifying risk factors for having sex with FSWs; and (3) comparing men's relationships with FSWs and non-FSWs in terms of relationship qualities and HIV-related risk behaviors, such as condom use. Structured interviews were conducted with a probability sample of 305 heterosexually active homeless men recruited from meal lines in Los Angeles. Recent sex with a FSW was reported by 26% of men, and more likely among those who were older, used crack cocaine, had more sex partners, believed that sometimes men just need to have sex no matter what, and were embedded in networks that were denser and where risky sex was more normative. Compared to non-FSW partners, men with FSW partners felt less emotionally close to them, were more likely to believe the partner had never been tested for HIV, and were more likely to have sex with them under the influence of drugs or alcohol; however, they were not more likely to talk about using condoms or to use condoms with FSWs. Whether the relationship was considered “serious” was a stronger correlate of condom use than whether the partner was a FSW. Implications of these findings for HIV prevention efforts among homeless adults are discussed.