This is a qualitative study of three children’s play activity and the concept of children’s play styles using the Children’s Developmental Play Instrument (CDPI). A brief summary description of the CDPI and the concept of play styles introduces the reader to the play scale. Two of the children’s play activity was previously rated as part of a larger quantitative study (N = 160) as manifesting attributes of the inhibited/conflicted play style. A third child was selected as a comparison example whose play activity was observed as predominantly manifesting the adaptive play style. Each child’s play activity is described in detail and analyzed using categories of the CDPI. Peer play and solitary play activity are discussed to illustrate individual differences in coping with the challenges confronting children at this age as they enter preschool. The authors use this issue to clarify the contributions of qualitative analysis to the understanding of play styles.