This study aimed at examining the correlation between personality factors measured by the HEXACO Model of Personality Structure - which defines the personality in terms of: Humility-Honesty H, Emotionality E, Extraversion X, Agreeableness A, Conscientiousness C, and Openness to experience O - and the level of personality functioning (LOPF). It also examines HEXACO’s predictability of LOPF in adolescence in terms of sex (male, female), birth order (eldest child, middle child, youngest child, and the only child) and financial levels (above average, on average, below average). The sample included 1450 students from both secondary schools and universities all over Lebanon. Participants responded to the HEXACO PI-R-60 scale of personality structure, and Level of Personality Functioning LOPF 2.0 that pinpoints to the degrees of dysfunctionality in both intrapersonal and interpersonal domains; participants also answered other demographic questions. Data were analyzed through SPSS 23 by calculating Pearson correlation coefficients, running ANOVA and post Hoc Hochberg GT2 and Dunett t tests to explore variance among subgroups. Independent T- tests were also utilized to determine sex differences. Multiple linear regression was utilized to determine the predictability of LOPF by HEXACO. Results show that HEXACO factors are inversely correlated to LOPF except for Emotionality; no significant differences in LOPF exist between males and females; on the financial level, differences in LOPF are found only between middle group and below average group, and in terms of birth order, between the only child and the middle child. It is also depicted that LOPF can be predicted by HEXACO factors in different ways. Implications of the study are discussed in the light of the related theories.