Data from the 1989 Communication Technologies cross-sectional survey of gay men in San Francisco indicate that both levels and correlates of sexual risk are different between younger and older gay men. Gay men under the age of 30 report higher risk behavior for human immunodeficiency virus (HIV) infection than do gay men who are 30 years of age or older. Further, the set of correlates of unprotected anal intercourse are different between younger and older gay men. Both young and old gay men report that having a primary partner and a lower perceived impact of the AIDS epidemic on their sexual behavior are associated with risk. However, among young gay men, reporting a lower attributed risk for HIV infection to unprotected anal intercourse, higher concern about AIDS risks, and shorter length of residence in San Francisco are positively correlated with risk-taking behavior. These associations were not statistically significant among gay men 30 years of age or older. It appears that the circumstances and/or reasons for taking sexual risk are different between older and younger gay men. Prevention programs must be designed so that they are sensitive to the needs of each generation of gay men.