Despite possessing knowledge regarding HIV transmission, many heterosexual college students engage in unprotected sex, partly because they lack necessary skills. The current study examined the assessment of safer sex skills, using roleplays. One hundred and fourteen undergraduates completed self-ratings of skills and participated in two written roleplays. Forty-one of them also participated in two videotaped roleplays. Results showed that students with different safer sex negotiation styles—assertive, aggressive, or compliant—used different persuasive arguments. Also, students used different arguments to persuade hypothetical relationship partners to engage in safer sex than they used with hypothetical one-night-stand partners. Finally, there was agreement across skills assessment methods—self-ratings, written roleplay ratings, and video roleplay ratings.