<p>Risky sexual behaviors (RSB) remain one of the major causes of unintended pregnancies and sexually transmitted infections. This study aimed to assess the prevalence of various RSB and their correlates among sexually active men in Rwanda, one of the poorest countries in the world. Using data from the 2020 Rwanda Demographic and Health Survey, a nationally representative sample of sexually active males (n = 4735) was examined for the prevalence of non-condom use, having multiple sex partners, engagement in commercial sex, and sexual debut before age 18. Multivariable logistic regression was conducted to explore 17 factors associated with various patterns of RSB. Results indicated that non-condom use, early sexual debut, multiple sex partners, and engagement in commercial sex were reported by 55.3%, 17.4%, 8.3%, and 7.3%, respectively. Older, married, and uncircumcised males with no internet access, and those from large female-headed households and the Western region, were more likely to engage in RSB without condoms (<i>AOR</i>: 1.28–6.20, <i>p</i> &lt; 0.05). In contrast, those engaging in RSB with condoms were less likely to be married and from the Southern region (<i>AOR</i> = 0.03 and 0.52, both <i>p</i> &lt; 0.05), but more likely to have a secondary education (<i>AOR</i> = 2.29, <i>p</i> &lt; 0.05). Those reporting an early sexual debut were more likely to be younger, unmarried, from large households, with no education, and non-Catholic (<i>AOR</i>: 1.24–2.72, <i>p</i> &lt; 0.05). There are differing groupings of Rwandan males that engage in various patterns of RSB that may partly reflect issues of access, changing cultural values, and geographic variations. These results indicate the need for segmented risk reduction interventions targeting each of these high-risk groups.</p>