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More than one half of sexually active teens have had sexual partners they are not dating. However, remarkably little is known about the nature of these sexual relationships. Using survey and qualitative data from the Toledo Adolescent Relationships Study the authors contrast the qualities of dating sexual relationships and sexual relationships that occur out-side the dating context. They find that adolescents having sex outside of the dating context are choosing partners who are friends or ex-girlfriends and/or boyfriends. Moreover, one third of these nondating sexual partnerships are associated with hopes or expectations that the relationship will lead to more conventional dating relationships. Boys and girls who experience sex outside of conventional dating relationships often share similar orientations toward their relationship. Results suggest that a more nuanced view is key to understanding adolescent sexual behavior.