At the dawn of the 21st century, both loneliness and homelessness are more pervasive than we would possibly like to admit. In this study, the experience of loneliness of the homeless was compared to that of the general population. Two hundred and sixty six homeless and 595 men and women from the general population answered a 30 item yes/no questionnaire. The experience of loneliness is composed of the following five factors: emotional distress, social inadequacy and alienation, growth and discovery, interpersonal isolation, and self-alienation. The present results indicated that the experience of loneliness for the homeless is significantly different than that of the general population. Gender main effects were explored and discussed.