The motion behaviors, rheological properties, and mechanical properties of a wax crystal mesoscale force chain network of waxy crude oil during gelation were experimentally studied and simulated by rheo-optic in situ measurement and computational fluid dynamics-discrete element method (CFD-DEM) numerical simulation, respectively. The motion behavior characteristics of wax crystals and the changes in the average coordination number of wax crystal networks were obtained at different temperatures. The study investigates the rule of crude oil rheological deterioration, the increase of wax crystals, and the changes in wax crystal motion behaviors with decreasing temperature. The relationship between the structure of the mesoscale force chain of the wax crystal network and the motion behaviors of the wax crystal and its rheological properties was analyzed. The results show that the average motion velocity of wax crystals or aggregates decreases from 28.48 to 22.56 μm/s when the temperature decreases from wax appearance temperature (48 °C) to 25 °C. The rotation and rolling trend of wax crystals gradually flatten, and the average coordination number increases 4.39 times. The viscosity of waxy crude oil increases from 6.27 to 8369.7 mPa·s, and the average coordination number of wax crystals obtained by CFD-DEM also increases significantly, which confirms the experimental results. We also found that when the system tended to gelation, a complex and stable force chain network was formed between the wax crystals, with a force chain coverage of 87.93% and a significant increase in the pressure drop in the flow field, which is consistent with the variation pattern of the system viscosity. The micro-meso-dynamic behavior analysis of waxy crude oil combined with CFD-DEM coupling provides a new way to explore the rheological properties of waxy crude oil and the microscopic mechanism of its modification.