Global reports indicate a steady increase in the number of people who are facing mental health concerns. Among those affected are students who struggle with balancing the demands of a hybrid learning environment. Recent studies are emerging on the use of chatbots as an accessible technology-based alternative to help address the challenges faced by school counselors in accommodating the influx of requests for consultations from students. This paper explores the potential in using a chatbot to provide a first-respondent service to help students maintain good mental well-being, a necessary precursor for individuals to practice self-care while reducing the risks of mental illnesses. We designed a chatbot that leverages storytelling strategies to assess the students’ well-being and to guide them in formulating actions necessary to sustain an optimal mental health. End-user validation captured students’ feedback regarding their perception on the support afforded by the chatbot from their three-day sessions. Expert analysis of the chatlogs revealed insights on the user expectations of the role of the chatbot and the impact of storytelling-based conversation flow in addressing support seekers’ needs toward sustaining positive mental health and well-being.