Prior research finds that sexually permissive individuals are judged more negatively than nonpermissive peers, placing them at risk of social isolation. Based on the positive assortment principle (i.e., preferences for similarity in attributes in close relationships), we examined whether participants’ own permissiveness mitigated negative judgments of permissive others in the same-sex friendship context. College students (N = 751) evaluated a hypothetical same-sex target with either 2 (nonpermissive) or 20 (permissive) past sex partners on 10 friendship-relevant outcomes. Participant permissiveness attenuated some negative evaluations. However, preferences were rarely reversed, and no moderation was found in five outcomes, suggesting the role of permissiveness-based positive assortment is limited, and evolutionary concerns may take precedence. Partial support for the sexual double standard was also found.