This study examined characteristics of men who use gay chat boxes on the Internet, including dating behaviour and sexual risk-taking with sex partners who were initially met through chatting. Men on chat boxes were asked to complete a brief questionnaire on the Internet. The questionnaire contained questions on demographics, chatting-related variables, and dating and risk-taking sexual behaviour. The results show that a large majority of the 190 respondents reported actual encounters as well as sex with men who were initially met through chatting. Almost 30% of the respondents who engaged in sex with chat dates reported inconsistent safe sexual behaviour. The level of unprotected sex increased as the number of sex partners who were met through chatting increased. These results suggest that chatters on the Internet may be a new target group for HIV prevention. Further study is needed to gain insight into the feasibility of prevention efforts for this target group.