The aim of this article is to analyse the motif of play appearing in early modern Dutch literature, from the perspective of the humanistic pedagogical ideas. These were humanist educators, such as Erasmus of Rotterdam and Juan Luis Vives, who started to recognize the pedagogical and educational benefits of game playing. The author discusses a manner in which the humanistic pedagogical ideals are reflected in the domain of the didactic literature, propagating ideal patterns of behavior. The paper addresses the mentioned problem by analyzing the phenomenon of play present in the one of the most popular Dutch didactic treatises Marriage (Houwelyck, 1625) of 17th-century poet and moralist Jacob Cats (1577–1660). It turns out that the motif of play presented in the treatise affects different contexts: educational, pedagogical and moral. Furthermore, the poet evaluates the concept of play by making a distinction between good and bad games. This division serves him as a metaphor of an ideal and non-ideal upbringing and parenthood. The analysis also shows that by recognizing the educational benefits of this form of entertainment, play, unless purposeful and useful, raises moral doubts, what, according to Jacob Cats and the mentioned humanist educators, has constituted its existence in the child’s world.