The primary aim of this study was testing the structure of adult playfulness in a joint analysis of seventeen questionnaires and testing the relation of the factors with the big five personality traits. A sample of 244 adults completed the questionnaires and a five factor-solution fit the data best; i.e., (a) Humorousness; (b) Cheerfulness–Uninhibitedness; (c) Expressiveness; (d) Other-directedness; and (e) Intellectuality–Creativity. Correlation analyses (bivariate, canonical) and regression analyses indicated strong overlap of the broader personality factors and the Cheerfulness–Uninhibitedness-factor (extraversion and emotional stability) as well as the Expressiveness-factor (extraversion). The study contributes towards a better understanding of the structure of playfulness in questionnaires developed for adults. Implications for future research are discussed.