Social problem-solving (SPS) is the balance that each person ought to have in order to cope with his/her major negative interpersonal events and consequently enjoys psychological well-being (PWB). The study aimed to investigate age and gender characteristics of SPS, negative orientation (NEGORI), major negative interpersonal events (MNIE), and PWB among 12-, 15-, and 18-year-old Hungarian and Palestinian adolescents. Furthermore, correlations between the previous variables were examined. The effects of family composition, parents’ education, MNIE factors, and PWB factors on SPSI factors were also explored. Some background factors were selected in this study (i.e., gender, age, family composition, and mother’s and father’s education). The following measurements were adopted: SPSI–R (D’Zurilla et al., 2022), NEGORI (Kasik et al., 2018), MNIE-M (Aburezeq & Kasik, 2021), and W-BQ12 (Bradley, 1994). The descriptive approach was adopted. The study included 661 Hungarian and Palestinian adolescents by the use of random stratified sampling. On the one hand, the Hungarian sample (n = 251) included boys (n = 109), girls (n = 142), 12-year-old (n = 93), 15-years-old (n = 86), and 18-years-old (n = 72). On the other hand, the Palestinian sample (n = 410) included boys (n = 201), girls (n = 209), 12-year-old (n = 124), 15-years-old (n = 127), and 18-years-old (n = 159). Based on the results, the following findings were revealed: Rational problem-solving was more typical among Hungarian 12-year-old girls. Negative problem orientation was found significant among Hungarian 15-year-old girls, while positive problem orientation was more typical among Hungarian 15-year-old boys. Positive problem orientation and rational problem solving were found to be typical among Palestinian 18-year-old girls. Fending off the problem, positive consequences, and waiting were more characteristics of Palestinian 12-year-old girls. MNIE related to family were significant in Palestinian 12-year-old boys. However, among Hungarian 12-years old, MNIE related to family were significant among boys. Among 15-year-old Hungarian adolescents, MNIE related to Classmates and yourself were more typical among girls. Among 18, Palestinian adolescent boys showed that they experienced MNIE related to classmates, teacher, and friends more than girls did. The findings of PWB reported that negative well-being was revealed as more typical among 18-year-old Palestinian girls. The findings of regression showed that there were multiple effects for the independent variables on the dependent variables.