In this study, we investigated the relationship between the four humor styles (Affiliative, Self-enhancing, Aggressive, and Self-defeating) assessed via the Humor Styles Questionnaire (HSQ) and the ten facets of the Big Five Questionnaire (BFQ) through network analysis. Four hundred and sixty-two Italian workers (61.3% women; Mage = 48.59; SD = 10.75) participated in the study and filled out the HSQ and the BFQ. Both centrality indexes (Expected Influence [EI]) and bridge nodes were calculated. In addition, the stability and accuracy of the network were checked. The network analysis revealed that HSQ Self-enhancing (EI = 0.63) showed the highest centrality among the HSQ styles, whereas BFQ Emotion Control (EI = 1.10) showed the highest centrality among BFQ facets; it also revealed that they were positively linked. Furthermore, HSQ Self-defeating emerged as the second-most-central humor style, negatively associated with BFQ Emotion Control. Concerning Bridge dimensions, four nodes were identified: HSQ Aggressive Humor, BFQ Emotion Control, BFQ Dynamism, and BFQ Dominance, with positive links between humor and personality except for Aggressive humor and Emotion Control, which showed negative links. On the basis of these results, the high centrality of HSQ Self-enhancing indicates the possibility of using this node as a starting point to foster positive and adaptive humor styles. The centrality of HSQ Self-defeating suggests that strength-based interventions could be focused to increase adaptive humor styles and to decrease them in order to enhance health-promoting humor styles. Furthermore, the bridge node of the HSQ Aggressive humor style with specific personality facets shows its possible use in intervention to both resize to adaptively improve relationships between humor and personality.