Positive effects of parent–child play have been documented but little is known about what drives this play. We observed eight-one children (kindergarten through 1st grade) of their play with the mother and father separately to determine how the play role of parents changed based on parent gender, child gender, and play context. Two significant 3-way interactions were identified: (1) parents of boys acted more often as directors in a puppet game, as facilitators in a building block game, and as co-players in a ball game, whereas parents of girls were more likely to be co-players in the puppet and building block games but facilitators in the ball game; (2) fathers tended to be directors more often than co-players in the ball game, while the opposite was true for mothers. Findings point to the important interplay of gender and context in determining the roles that parents enact when playing with children.