Objective: To determine whether the main reason for bedtime is associated with sleep and adaptive functioning in adolescents. Methods: Participants were 1374 adolescents (X age = 16.8 years, SD = 0.58; 33.6% male) from Helsinki, Finland. Adolescents completed a questionnaire battery including the Munich Chronotype Questionnaire, Strengths and Difficulties Questionnaire, Beck Depression Inventory, and items drawn from the School Sleep Habits Survey, and the Pittsburgh Sleep Quality Index. Results: On school nights, adolescents whose parents set their bedtime, and those who went to bed when they were tired went to bed earlier, obtained more sleep and had earlier midpoint of sleep than adolescents who went to bed when they have finished messaging/socializing or when their television show had finished. Adolescents who went to bed when they had finished their homework had sleep that fell in between these groups. On weekends, adolescents whose parents set their bedtime went to bed earlier and had an earlier midpoint of sleep. However, there were no differences between groups in terms of sleep duration once the need to rise for school in the morning was removed. Adolescents who went to bed on school nights when they were tired or once their homework was finished had better adaptive functioning. Conclusions: These results provide support for two very different approaches to help optimize the sleep of adolescents: either by implementing parental regulation of bedtimes across adolescence, or by encouraging adolescents to use their bodily cues to indicate when it is time for bed, rather than relying on an external cue.