This paper connects three concepts that emerge in contemporary society, and thus in contemporary childhood. The first concept is overprotection of the child, that is, creating a context in which potential risk situations are avoided and characterized as undesirable. In such an environment, we take away the opportunity to examine their own choices and the experiences from children which is characteristic of another concept, which is called "risky play". In a "risky game" the child tests his or her options and boundaries, copes with stressful situations and creates methods of coping with and dealing with such situations. From desirable outcomes from stressful situations, the child creates positive experiences and later in his or her adulthood is more competent to deal with stressful situations. It is this phenomenon that describes the third concept in this paper, which is resilience. This paper seeks to explore the relationship between gender, income, parental and educator education levels, and educators' work experiences with attitudes toward "risky play." The study was conducted on a sample of 316 respondents, of which 279 were parents and 37 educators. An instrument used in the research was the "Tolerance to Risk in Risky Play Scale" (TRiPS), which contains questions describing activities for children which are used to test adult tolerance of risk in children's play. The study found statistically significant differences between parents and educators attitudes toward risky play. Also, there was a statistically significant difference in the domain of self-rating own attitudes toward “risky play” with respect to education of the respondents.