As a clinical condition, boredom is an emotional state, widespread among young people, characterized by unpleasant feelings, lack of motivation, and low physiological arousal in which the level of stimulation is perceived as unsatisfactorily low. Boredom is an important emotional state due to its spread among young people. Recent research has mainly studied the complex connection between boredom and leisure-time experiences, which may be involved in adolescents’ risk-taking behaviors. The current study aims to investigate boredom proneness, conceived as a personality trait, in adolescents’ free time, and its involvement in more extreme behaviors, such as binge drinking and addictive Internet use, which may represent ways to cope with the search for additional stimuli. Data from a large sample of Italian adolescents (n = 478, aged between 14 years and 19 years, M = 16.31, SD = 1.47) revealed significant differences between low-boredom and high-boredom subjects. Both girls and boys with high boredom proneness used technology more, engaged less in hobbies and activities such as sports, more frequently consumed strong drinks and binge drank, and were more at risk of Internet addiction than non-bored adolescents. These findings suggest a hypothetical risk profile linked to boredom proneness in adolescence. The results are discussed in light of the literature from a psychosocial and clinical perspective.