Freud''s enthralling relationships with Fliess and Ferenczi are examined in the light of the preoedipal fixation in his personality development. Theoretical exposition of the preoedipal phase and the corresponding stalemate, as well as Freud''s own early childhood, are delineated as the background of this study. The primary sources of data are mainly Freud''s correspondence with these two persons, as supplemented by biographical materials. Patterns of interaction and repetition are extracted to illustrate Freud''s preoedipal impasse. Implications on Freud''s life and work are discussed in light of this developmental arrest.