A printing assist system including a print mode storage storing a plurality of print modes each including a specification of a printed material and a setting of a printing device, means for acquiring print specification information, means for acquiring printing device capability information, means for retrieving a plurality of print modes based on the acquired print specification information and the acquired printing device information, means for calculating, for each of the print modes retrieved by the print mode retrieving means and for each of a plurality of evaluation items, an evaluation value relative to other print modes, a selection history storage that stores a history of print mode selection by a user and includes the evaluation value of the present print mode for each evaluation item, and means for offering the plurality of retrieved print modes based on the selection history information and the evaluation values.