With the evident emergence of social media and the internet, it is crucial to acknowledge their potential to play a significant role in the self-esteem of high school students. This study was conducted to explore students' reflections on social media and further understand their varying experiences and reflections about the subject. Six students from Bacolod Trinity Christian School were chosen and subjected to semi-structured interviews. Responses from the interviews were then analyzed through thematic analysis, enabling researchers to recognize the findings to the answers to the study’s questions. The themes of the findings shows that: (1) Social media significantly affects high school students’ self-esteem either positively or negatively, (2) Social comparison fosters discontentment in different aspects of oneself in favor of higher, often unrealistic standards, (3) Cyberbullying fosters insecurity in victims and fear in the online space, (4) Positive social engagement on social media improves self-esteem, but the absence of such does not affect it, (5) Offline interactions and activities with a stronger sense of self mitigate social media’s negative effects. Amongst the data gathered, parallels and patterns can be found among the respondents despite the differences in stories and experiences. Each piece of content was then evaluated and thought through thoroughly to provide clear insight into the recommendations and conclusion of the study.