Embodiments relate to systems and methods for electronically booking ride share trips. The systems and methods can involve a data storage device storing ride sharing records with itineraries including a plurality of legs. The systems and methods can involve at least one processor configured to receive a trip booking request for a passenger, the trip booking request defining passenger constraints including a desired pickup time or drop off time. The at least one processor is configured to generate trip booking options from available ride sharing itineraries, each trip booking option including a leg that satisfies the passenger constraints of the trip booking request. The at least one processor is configured to compute objective values for the trip booking options and remove at least one trip booking option based on a comparison of its objective value and temporal proximity to at least one other trip booking option. The at least one processor is configured to transmit the retained trip booking options for display and confirmation at an interface application of an electronic device.