The present study aimed to investigate the importance of self-esteem for sociosexual orientation and to compare groups of dating online users in terms of engaging in casual sex, performed in one night stand (ONS) and friends with benefit (FWB). This issue seems particularly important in the context of psychosexual health. The exploratory study was conducted online among 416 adults who have participated in online dating. The Rosenberg Self-Esteem Scale (RSES), the revised Sociosexual Orientation Inventory (SOI-R), the author’s questionnaire, concerning having experiences in ONS and FWB, and motives for entering into expected types of relationships were used. The Kruskal-Wallis H test with post hoc pairwise comparisons. A statistically significant negative correlation between self-esteem and sociosexual orientation concerned the sociosexual attitude subscale. Differences were found between those engaging in ONS and FWB types of relationships. Those who engaged only in FWB had lower SOI-R scores than those who had only ONS experiences and both. Such results suggest that these relationships should be considered to be disparate and different functions should be attributed to them. Given the differences, it will be possible to use these results to support the design of public health interventions and reduce online sexual risk behavior.