Blossom is a prototype mobile application that proactively monitors mental health among students to detect mental health issues and encourage them to reach out early. Through monthly surveys used in professional mental health settings, Blossom highlights irregularities or negative trends to students and prompts them to schedule an appointment with the school counselors for thorough assessment. In addition, a sharing platform is included for students to talk about their experience in recognizing and coping with mental health issues. Blossom aims to facilitate a more proactive approach to mental health in Singapore schools, and create a conversation to destigmatize the topic.