Investigation of a lubrication behavior of phase change materials (PCM) can be challenging in applications involving relative motion, e.g., sport (ice skating), food (chocolates), energy (thermal storage), apparel (textiles with PCM), etc. In oral tribology, a phase change often occurs in a sequence of dynamic interactions between the ingested PCM and oral surfaces from a licking stage to a saliva-mixed stage at contact scales spanning micro-(cellular), meso-(papillae), and macroscales. Often the lubrication performance and correlations across length scales and different stages remain poorly understood due to the lack of testing setups mimicking real human tissues. Herein, we bring new insights into lubrication mechanisms of PCM using dark chocolate as an exemplar at a single-papilla (meso)-scale and a full-tongue (macro) scale covering the solid, molten, and saliva-mixed states, uniting highly sophisticated biomimetic oral surfaces with in situ tribomicroscopy for the first time. Unprecedented results from this study supported by transcending lubrication theories reveal how the tribological mechanism in licking shifted from solid fat-dominated lubrication (saliva-poor regime) to aqueous lubrication (saliva-dominant regime), the latter resulted in increasing the coefficient of friction by at least threefold. At the mesoscale, the governing mechanisms were bridging of cocoa butter in between confined cocoa particles and fat coalescence of emulsion droplets for the molten and saliva-mixed states, respectively. At the macroscale, a distinctive hydrodynamic viscous film formed at the interface governing the speed-dependent lubrication behavior indicates the striking importance of multiscale analyses. New tribological insights across different stages and scales of phase transition from this study will inspire rational design of the next generation of PCM and solid particle-containing materials.