This chapter seeks to demonstrate that one of the most prominent Luhmann’s Social System – culture – boasts a paramount importance on the breadth and scope of the second tier of the Four-Tiered Model of Mediation, which is the Cultural Dynamics of Mediation. A central claim stands out in this regard: leveraging on, a drawing on, a wide range of empirical studies gleaned/harvested on the soil of Applied Psychology, Sociology and Anthropology, the styles of mediation should be bespoken to the disputants’ cultural background, individuality, legal culture and legal tradition or cultural divergence with law may otherwise occur.