The present study aimed to examine the psychological factors of perceived self-efficacy, peer group pressure, and family connectedness in relation to sexually risky behaviors and sexual permissiveness among Undergraduate students in the Ibadan metropolis. The current investigation used a cross-sectional research strategy and surveyed 327 randomly chosen first-year students from the University of Ibadan. Out of the total sample size, 169 individuals (51.7%) were identified as males, and 158 individuals (48.3%) were females. Data was collected via a self-report questionnaire with standardized scale items measuring peer pressure, self-efficacy, and family connectedness. The formulated hypotheses were tested using inferential statistics at a 0.05 significance level. The findings of this study indicate that self-efficacy, peer group pressure, and family connectedness collectively exert a substantial impact on risky sexual behavior. Specifically, peer group pressure exhibited a positive relationship with risky sexual behavior, while family connectedness demonstrated a negative. The analysis of the primary variables in this study demonstrated a significant and positive association between self-efficacy and risky sexual behavior, as well as between peer group pressure and risky sexual behavior. There is a need for further investigation into psychological variables as potential indicators of risky sexual behavior, given the growing prevalence of sexual engagement among adolescents and young adults.