A system for and a method of determining that a detoured trip is to be presented to a potential passenger. The method comprises receiving a rideshare request; generating a rideshare request parameter; and accessing, from a database, trip filtering parameters associated with trips. The method further comprises determining that at least one of the trips is a candidate for which a detour route is to be computed based on an analysis of the rideshare request parameter and a corresponding trip filtering parameter associated with the at least one of the trips; causing to compute, for the at least one of the trips determined as being the candidate for which the detour route is to be computed, a detoured trip; and determining that the detoured trip is to be presented to the potential passenger by analyzing the deviation value of the detoured trip and the deviation threshold.