The number of adolescent pregnancies in the United States has reached epidemic proportions. Loneliness and adolescent sexuality, however, have not been previously studied. This descriptive study investigated the relationships of characterological and situational loneliness in childbearing adolescents. Related variables of shyness, self-esteem, perceived maternal and paternal expressiveness, and social support also were studied. The data were collected at multiple sites in Northern California using a convenience sample of adolescents ranging in age from 12 to 21 years: early (n = 11), middle (n = 22), and late (n = 24). Results of the analysis of variance and the Tukey-HSD indicated situational variables were more significant than characterological variables in understanding loneliness in early and middle adolescence. The characterological variables were not statistically significant. Using Pearson's correlation coefficient, significant relationships were found among and between variables. The findings suggest parental relationships were powerful in influencing the existence of loneliness as well as self-esteem, shyness, and social support.