Comprehensive sexual health education is critical for the prevention of STIs and unintended pregnancy among young people. Yet, increasing barriers to comprehensive sexual health education in classroom settings underscore the importance of youth-friendly technologies to address sexual health among young people. "It's OK to Ask Someone" (IOTAS) uses a customised technology to expand Planned Parenthood of Western Pennsylvania's sexual health programming with a confidential sexual health textline designed to answer sexual health questions in a timely, user-friendly manner. This paper describes results from a process evaluation focused on assessing who uses IOTAS, how they use IOTAS and in what ways IOTAS is perceived to be helpful to texters. Results illustrate that a textline-approach is an acceptable and appropriate way to engage with young people. Findings demonstrate that young people are using the confidential textline to seek information about sexual health and report it as a helpful resource. Findings are relevant for sexual health educators and practitioners working with young people, including those interested in using a technology approach to expand health education opportunities. Additional research should continue to explore the potential of youth-friendly, technology-based approaches to support sexual health information seeking.