In this article, we highlight how adults remain emotionally involved with transitional objects, such as stuffed animals, carried over from their childhoods. Drawing on focus groups involving undergraduate students enrolled in teacher education and childhood studies programs, we found that the participants' reflections of their stuffed animals opened onto layered meanings: 1) tactile experiences of materiality and sensation; 2) personal memories of innocence and paternal protection; and 3) conceptualizations of uncertainty and anxiety in adulthood. While we found that stuffed animals can be important access points to underrepresented feelings of vulnerability in adulthood, we also noted that these transitional objects can be used to entrench normative notions of teaching, development, and childhood. We suggest that transitional objects can be resources in fields devoted to the well-being and growth of children, especially as they help prospective teachers work through the ambivalences and defenses that accompany the work of education and care.