The imaginative figuration or categorical imperative of not using another as mere means but viewing him/her as an end in him/herself becomes the key for filling out and giving substance to the blurred sketch of freedom in Kant’s moral philosophy. Kant cannot maintain entirely his position of transcendental freedom without revisiting and expanding his notion of the productive imagination and returning to his ‘Shakespearian’ anthropological sensibilities, especially in the context of his later moral philosophy in The Metaphysics of Morals. Moral sociable sociability is a cultivation of reciprocity, agreeableness, tolerance, mutual love and respect. Friendship is Kant’s primary and privileged category in this context, and it is a key practice of personhood and moral sociable sociability. It is the conjunction of respect and benevolence or mutual love. The conjunction entails that love draws two people together and respect keeps them at a proper distance. There is neither mergence nor repulsion but respectful distance; there is neither mutual self-interest nor advantage or disadvantage, but mutual trustworthiness and generosity of spirit.