This study investigated the extent to which negative emotions, personality traits, and obsessive-compulsive distress modulate the relationship between sleep problems and dream experiences. The sample consisted of 610 upper secondary school students, whose subjective intensity of dream experiences, thematic dream content, obsessive-compulsive distress, personality traits, defensiveness, emotional qualities, and sleep disturbances were assessed using the Dream Intensity Scale, Dream Motif Scale, Obsessive-Compulsive Inventory-Revised, NEO Five-Factor Inventory, Marlowe-Crowne Social Desirability Scale, Beck Depression Inventory-II, Beck Anxiety Inventory, State-Trait Anger Expression Iventory-2, and Sleep Habits Questionnaire. The overall findings indicate that waking-life emotionality, personality traits, obsessive-compulsive distress, and other important factors for sleep quality – such as the ability to unwind one’s mind when retiring to sleep – moderate but do not mediate the relationship between disrupted sleep and dreaming. It seems, therefore, that dream experiences can serve as unique indicators of sleep problems.