In times of rapid urbanization, the mental health and the psychological well-being of the citizens are recognized as a challenge. Much research has been conducted on the mental health and psychological well-being of the people, but none about the Lebanese population. To get an insight into the urbanization (urban growth, moving to cities) and urbanicity (different settlement sizes) association with mental health and psychological well-being of the Lebanese people, a questionnaire to 515 Lebanese citizens was conducted. The study showed large city dwellers being more nervous, less excited, but more hopeful about the future, less worried, and with less suicidal thoughts than small cities and rural dwellers; while rural dwellers are, on average, more sad, depressed, and lonely than those in large and small cities, however, urban dwellers being “always/most of the time” sad or depressed are in a percentage higher than rural dwellers.