Studying play behavior in octopuses is an important step toward understanding the phylogenetic origins and function of play as well as the cognitive abilities of invertebrates. Fourteen Octopus vulgaris (7 subadults and 7 adults) were presented 2 Lego objects and 2 different food items on 7 consecutive days under 2 different levels of food deprivation. Nine subjects showed play-like behavior with the Lego objects. There was no significant difference in play-like behavior corresponding to food deprivation, age, and sex of the octopuses. The sequence of behaviors, from exploration to play-like behavior, had a significant influence on the establishment of play-like behavior, as it occurred mostly on Days 3–6 of the 7-day experiment. The pattern of development of play-like activities after a period of exploration and habituation in this study agrees with the hypothesis that object play follows object exploration. A homologous origin of this behavioral trait in vertebrates and invertebrates is highly unlikely, as the last common ancestor might not have had the cognitive capacity to possess this trait.