Most theories about the cultivation of virtue fall under the general umbrella of the role model approach, according to which virtue is acquired by emulating role models, and where those role models are usually conceived of as superior in some relevant respect to the learners. I will argue here that although we need role models to cultivate virtue, they are not sufficient. We also need good and close relationships with people who are not our superiors. I draw special attention to the notion of character friendship as conceived by Aristotle, as an antidote for the common misleading overemphasis on role models. My primary goal is to show how much we stand to gain by including character friendship in our account of virtue cultivation. Friendship is a close relationship characterized by mutual appreciation, well-wishing, and mutual acknowledgment of such appreciation and well-wishing. Character friendship is a friendship grounded in the mutual appreciation of the friends’ good characters, and a basic agreement and concern for the good. I hope to show here that such a relationship (a) constitutes a unique form of experience in which we share or inhabit a substantial way of seeing with a close other; (b) facilitates a unique form of knowledge, the knowledge of a particular person (my-self and the other’s self); (c) develops other emotions important for the cultivation of virtue besides admiration, such as love, shame, trust, and hope; and (d) is a praxis in which cooperative interactions and discussions function as a bridge between habituation of virtue at home and public life. Character friendship is an experience which provides necessary elements for human cultivation of virtue that the sole experience of having a role model does not. There is empirical evidence that seems to give at least some indirect support to my thesis. According to developmental and social psychology, friendship in general is fundamental for human (moral and cognitive) development from a very early age. There are also good reasons to think adolescents know what a good friend is, an exhibit aspiration to be good friends and engage in what we call character friendships. As a consequence of this, I argue greater emphasis should be placed on the role of friendship in the context of character education. We, as adults, should acknowledge, care, and facilitate children’s and adolescent’s friendships within schools and homes, and implement some practical strategies to help them foster character friendships.