This paper aims to show a possible path to address the introduction of intimate digital technologies through a phenomenological and postphenomenological perspective in relation to Japanese and Chinese contexts. Digital technologies are becoming intimate, and, in Japan and China, there are already many advanced digital technologies that provide digital companions for love relationships. Phenomenology has extensive research on how love relationships and intimacy shape the subjects. At the same time, postphenomenology provides a sound framework on how technologies shape the values (...) and meanings we have. Thus, this paper introduces two digital technologies in Japan and China (_Love Plus_ and _XiaoIce_ chatbot), and it analyses according to the elements proposed by phenomenology and postphenomenology. In conclusion, this paper shows how digital companions like _Love Plus_ and _XiaoIce_ chatbot change who we are and the values and meanings we have according to the phenomenological and postphenomenological framework. These entities might not be human, but they shape who we are as human beings and the meanings and value we give to love. (shrink)