Sexting and sending nude and semi-nude photographs continues to be at the forefront of discourse pertaining to adolescence. While researchers have explored consequences for sexting, less is known about the challenges adolescents face when making decisions about sending photographs. Using online personal accounts posted by adolescents, this study explores young women’s reported dilemmas with sending nude photographs to their peers. A thematic analysis of 462 stories reveals that young women received conflicting messages which told them both to send and refrain from sending photographs. In addition to sending photographs in the hope of gaining a relationship, young women also reported sending photographs as the result of coercion by male counterparts in the form of persistent requests, anger, and threats. Young women attempted to navigate young men’s coercive behaviors yet frequently resorted to compliance. Refusal was often met with repeated requests or threats. Alternative tactics were largely absent from young women’s stories, indicating that young women do not have tools to successfully navigate the challenges they face. (PsycINFO Database Record (c) 2019 APA, all rights reserved)