A request pick-up assisting system includes: a question information registering unit registering a question item and attributes of a questionee; a basic connection word candidate extracting unit referring to information that includes words of the question, and extracting words that coexist with the words of the question; an attribute connection word candidate extracting unit referring to information including words of the question, and information that includes words constituting attributes of the questionee, and extracting, for each attribute, words in which the words of the question and the attributes coexist; an attribute specificity calculating unit calculating an attribute specificity based on dissimilarity between groups of words; an effective attribute extracting unit comparing attribute specificity for each attribute, and extracting a suitable attribute; a connection word extracting unit extracting a connection word about the effective attribute; and an association chart creating unit generating an association chart, by referencing the extracted connection word.