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Self-regulation is essential to youths’ long-term mental well-being and healthy functioning and positive anticipation of future events may support healthy emotional regulation. Green Chimneys, a school in New York that serves students with special education needs and psychosocial challenges, offers its students weekly one-on-one nature-based mentoring sessions with school staff. We used a modified version of the State Difficulties in Emotion Regulation Scale (S-DERS) to explore how these sessions impacted students’ emotional regulation both before and after their sessions. Results indicated that students’ behavior may improve in the 1-4 hours prior to participation. Further research is needed to test these findings.