This chapter chronicles a collaboration that brought together adolescent boys in foster care and adult women residing in a homeless shelter through the reciprocal creation of handmade gifts. Members of these two populations often have histories of trauma and attachment disruption. This symbolic dialogue was intended to model participation in a positive mother-child interaction to benefit both groups through the giving and receiving of transitional objects. These gifts took the form of dolls, stuffed animals, blankets, pillows, and handwritten notes. This chapter closes with a review of best practices for and other examples of art therapy directives that promote resilience and altruism in children living in residential foster care.