The study analyzed the sources, experiences, and insights in speaking English comfortably among Grade 10 students at La Filipina National High School, Philippines. Phenomenological qualitative research design was used to gather data from 10 learner-informants. The findings revealed that students sources of being comfortable in speaking English is influenced by a number of sources of confidence brought by parents, classmates and teachers. Students describe their experiences as being helped by teachers by providing strategies to improve English speaking skills and be comfortable with it. They also provide insights and recommendations for other students to develop speaking skills. Students identify reinforcement programs and ways how stakeholders could help them develop their speaking skills. The researcher suggests the creation and strengthening of academic programs to promote a supportive and inclusive environment, encourage a positive mindset, and provide ample practice facilities, such as speech and reading laboratories, classrooms with information technology and area for speech performances. These can help students communicate, connect with others, and succeed in various personal, academic, and professional contexts.