This contribution explores the relationship between familiarity and habit employing Dewey’s and Merleau-Ponty’s insights as theoretical tools. Although the two notions are  closely related to each other, their relationship seems to have been overlooked by research. Therefore, in the attempt to start filling the gap, the article shows some aspects (and problems) of the functioning of their mutual interweaving. The argument focuses on habit in the first section, then moves to familiarity in the second, finally coming to the relation between the two, developing some key points and ideas which have emerged along the way. Dewey’s and Merleau-Ponty’s philosophies offer many helpful pointers to accomplish the task. Particularly, the notion of knowledge of familiarity introduced by the French philosopher seems to be significantly relevant.