An information processing apparatus includes an information acquisition unit that acquires first text information handled in a terminal apparatus of a first user in response to a search request issued by the first user to search for candidate users from among a plurality of users. There is a condition generation unit that divides words included in the first text information into a first word group having an appearance frequency lower than a first threshold and a second word group having an appearance frequency equal to or higher than the first threshold according to an appearance frequency in second text information related to past work of the first user. Further, there is a search processing unit that extracts the candidate users from among users according to an appearance frequency of a word belonging to the first word group in third text information related to past work of each user.