Context matters in learning experiences. Situating learning within relevant contexts and allowing all learners to feel more connected to the content can benefit learners, especially when learning complex computing concepts. Generative AI presents an opportunity to quickly craft relevant learning experiences, but also presents risks. As teachers are exploring generative AI for lesson planning and various course content creation, there is a need to strategically discuss the implementation of pedagogical practices through generative AI. This special session invites participants to engage in an interactive and collaborative journey into learner-relevant computing education in the age of generative AI. Through interactive demonstrations, hands-on exercises, and guided discussion, participants will explore strategies to generate meaningful learning examples, practice prompt engineering for contextualized learning, and critically evaluate AI-generated content for relevance and potential bias. This session will equip educators and researchers, with practical tools for integrating learner relevant generative AI content responsibly into computing education.