The literature shows that teachers’ psychological characteristics can influence adolescents’ mental health. Additionally, neuropsychopedagogical interventions, like the Envisioning the Future (EF) training, can positively impact wellbeing. The study aims at: (i) exploring the relationships between teachers’ and students’ characteristics and (ii) investigating the impact of EF on students’ wellbeing. The sample consists of N = 113 Italian adolescents, whose data were matched with their teachers’ (N = 12). Participants completed validated self-report questionnaires on self-compassion, emotion regulation, resilience, and an ad-hoc scale of frequency of bullying episodes. Correlational analyses highlight that: teachers’ avoidance, social isolation, and self-judgment negatively correlate with the frequency with which students perceive bullying episodes; teachers’ self-kindness, optimism, and self-efficacy in regulating emotions positively correlate with the frequency with which the students’ perceive bullying; teachers’ cognitive focus positively correlates with students’ self-determination toward future decisions; students’ self-judgment negatively correlates with teachers’ resilience and self-efficacy in managing positive emotions, while it positively correlates with teachers’ avoidance. In addition, after EF training, students had improved in negative emotion regulation, frequency of perceiving bullying, common humanity, and self-determination. The study underscores the importance of the relationship between teachers’ and students’ resources and the impact of EF training on adolescents’ wellbeing.