Systems and methods for guided vehicle matching are disclosed. In order to generate vehicle recommendations for a user of an electronic vehicle listing service, a plurality of vehicle-related lifestyle options are presented to the user, and a user selection received. Additional data regarding the user's vehicle preferences, requirements, or usage may be obtained. Based upon such information, a set of example vehicles is generated and presented to the user. Each example vehicle has characteristics representing a plurality of other vehicles. Based upon user ratings or selections of at least some of the example vehicles, a plurality of vehicle recommendations for specific available vehicles are generated and presented to the user. In some embodiments, further user interaction with such recommendations is used to refine the vehicle recommendations and identify additional vehicle recommendations.