Risk factors associated with the likelihood of being sexually victimized by a stranger or friend/acquaintance since being on the street was examined among 372 homeless and runaway youth. Young people were interviewed on the streets and in shelters by outreach workers using a systematic sampling strategy. Youth who engaged in more high-risk behaviors were expected to be at greater risk for sexual victimization by both known and unknown assailants. Results indicated that for females, running from home for the first time at an earlier age was associated with sexual victimization by both a stranger and friend/acquaintance. However, engaging in deviant subsistence strategies, survival sex, and grooming predicted being sexually victimized by a friend/acquaintance. For males, survival sex and grooming predicted stranger sexual victimization, whereas sexual orientation was associated with sexual victimization by a friend/acquaintance. Overall, 35% of the sample had been sexually victimized.