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This paper reports on the breaking of agreements between regular partners among HIV-negative gay men in Sydney. Data were from the 1333 men completing face-to-face interviews through December 2003 for the Health in Men (HIM) open cohort of HIV-negative gay men in Sydney. 822 men had a primary regular partner during the six month period before their 2003 interview. Most of these men had entered into agreements with their partners about sex either with each other or with other partners (87.2%). They most commonly agreed not to use condoms with each other (50.6%). Regarding casual sex, they most commonly agreed to always use condoms (34.2%) or to have no sex with men outside their relationships (28.6%). 48.8% reported some discomfort discussing with their partner their sex outside the relationship. Among those with agreements with their partners, 27.7% reported ever breaking those agreements. Those who found it more difficult to discuss issues of HIV serostatus and sexuality were more likely to report having broken their agreements (p <.001; p = .021 at one-year follow-up) and were more likely to have engaged in unprotected anal intercourse with casual partners (p <.001). A third of those men who broke their agreements did not inform their partner. A substantial proportion of gay men with agreements with their regular partners report some discomfort discussing sexuality and HIV serostatus with their partners. Difficulty discussing these issues may place these men at increased risk of breaking their agreements and may place both themselves and their partners at increased risk of infection.