Taking a socio-cultural perspective, in this study we explored the challenges toddlers might face as they practice 1–1 correspondence in the playful context of setting a table, and how different individuals may participate in this playful activity. Findings indicated that toddlers’ competence in carrying out one-to-one correspondence may be related to the locations of items set on the table and what to do with leftover items. The researcher played several roles including the expert participant, assistant, and play partner. Some toddlers participated peripherally, others were more involved in the play, while others were more involved in completing the 1–1 correspondence. In some instances, it seemed that a child’s participation was an interference, rather than a help. Toddler educators may consider how natural settings and activities may be adjusted to offer children appropriate playful mathematical learning experiences.