This research is an examination of the relationship between loneliness and a number of psychosocial variables (e.g., affective state, cultural issues, gender, age) among adolescents and young adults from Cape Verde and Portugal. Two studies are presented. The participants in the first study were 285 adolescents from Cape Verde and 202 from Portugal, and in the second study there were 134 college students from Cape Verde and 112 from Portugal. The following instruments were administered to all the participants in both studies: The Revised UCLA Loneliness Scale (D. Russell, L. Peplau, & C. Cutrona, 1980), the Neuroticism Scale (J. Barros, 1999), the Optimism Scale (J. Barros, 1998), the Social Anxiety subscale (A. Fenigstein, M. Scheier, & A. Buss, 1975), and the Satisfaction With Life Scale (E. Diener, R. Emmons, R. Larsen, & S. Griffin, 1985). No ethnic or gender differences were found for loneliness between the two groups. For both groups, the most prominent predictors of loneliness were neuroticism and dissatisfaction with life. However, as expected, the adolescent group recorded higher scores for loneliness than did the college students.