This study set out to examine how toddlers’ word learning, imitation, and instrumental helping would be affected by the emotional reliability of a familiar model. Therefore, forty-two 24-month-olds were observed in interactions with their primary caregiver, who was evaluated on the quality of his or her sensitive behavior, such as responsiveness and emotional availability. Parents were first instructed how to administer different tasks to their child that included: teaching a novel word, demonstrating an “irrational” means of putting a dog inside a toy house through the chimney instead of the door, and appearing in need of help. The parent-child dyad was then observed during a 10-min period and the parent’s level of responsiveness and availability was subsequently coded from this interaction. Finally, children were examined as to whether they learned a novel word, imitated, and helped their caregiver. It was observed that toddlers learned novel words better from an emotionally reliable primary caregiver. In addition, higher parental responsiveness and availability predicted better imitation in older children and higher levels of helping in girls. Taken together, these findings are the first to suggest that the emotional reliability of a familiar model, such as a parent’s sensitive nature and consistent responsiveness, influences young children’s willingness to learn and help.