Jamaica is home to over 10% of the Caribbean’s HIV-positive population. Men who have sex with men (MSM) have a higher prevalence of HIV compared to the general public. Thus, the purpose of this study is to assess characteristics associated with HIV, such as condom use and number of sexual partners, comparing young, those aged 18–24, to older, aged 25 and older, MSM in Jamaica. We hypothesised, and found support for the notion, that younger MSM would have a lower rate of some risky behaviours associated with HIV seropositivity. Service data for 160 self-selected MSM aged 18–62, from Kingston, Jamaica were analysed. The majority identified as homosexual (compared to bisexual), over half of respondents completed a tertiary level of education (e.g. any post-high school training), and 59.1% were employed. Almost all participants reported agreeing to use a condom when requested (93.6%). Prevalence of HIV was 17.8%, much lower than the 32% found in national studies, and is likely an underestimation reflecting patterns of this self-selected sample. Additionally, over one-third reported experiencing sexual abuse. Statistically significant relationships were found between age group and tertiary education, employment status, condom use with a regular partner, and sexual abuse. Younger MSM were more likely to have been sexually abused and were more likely to always wear a condom with their regular partner. A limitation of this study was the extent of missing data, restricting generalisability. However, by acknowledging the heterogeneity of the Jamaican MSM population, and subsequently evaluating behaviours across age groups, nuances emerge which highlight behavioural diversity. Findings may inform public health practitioners in developing targeted interventions.