A vehicle drive assistance system is provided, which includes a processor configured to execute an individual driver model learning engine configured to build an individual driver model unique to a vehicle driver based on driving data of the driver, and an on-board controller provided in a vehicle of the driver and configured to perform particular vehicle control processing. The individual driver model learning engine analyzes a current state of the driver based on the driving data, determines recommending processing that corresponds to the analyzed state based on the individual driver model, and instructs the on-board controller to perform the recommending processing.