The virtually nonexistent dialogue between biblical studies and Orthodox theology should not lead us to dismiss its possibility. Here the category of personal relationship is explored in the thought of the Apostle Paul. It is emphasized that personal relationship should not only be understood as communication between different parties but also as apprenticeship, simulation, and even identification, not only on the level of behavior but also on a deeper level of organic unity. It is argued that for Paul, the theological concept of imitation (“be imitators of me as I am of Christ”) is a corollary of personal relationship or, conversely, personal relationship is a prerequisite for imitation in its theological meaning. Therefore, apprehending this concept is crucial for the clarification of the meaning and the significance of personal relations in Paul.