Condom negotiation skills are critical for safe sexual encounters; yet, factors such as intimate partner violence (IPV) may affect an individual's effectiveness or ability. The current analysis examined the association of past experiences of IPV on participants' sexual assertiveness, condom insistence, and sexual risk taking intentions. Participants (177 heterosexual women, 157 heterosexual men, and 106 men who have sex with men [MSM]; all participants were single or in a new/casual relationship and between the ages of 18–25 years old) read a vignette describing a sexual encounter with a hypothetical new partner who insists on having sex without a condom. Sexual assertiveness was not significantly associated with IPV. However, participants (particularly MSM) who reported any past IPV were significantly more willing to agree to condomless sex compared to those who reported none; as were participants who experienced physical IPV only compared to those who reported psychological IPV only. These findings suggest that MSM and individuals who have experienced physical forms of IPV may need additional support and training to stand-up to a sexual partner who is resistant to condom use.