A ride-share system of other vehicle system employs a profile database having a plurality of user phobia profiles for potential customers. Each of the user phobia profiles identifies one or more respective phobia groups pertaining to a respective user, wherein each phobia group associates a plurality of driving-related phobias which share at least one trigger condition or at least one countermeasure. A vehicle controller is coupled to the profile database which determines a default itinerary for a trip to a destination specified by one of the users. The vehicle controller evaluates the default itinerary for potential interaction with a respective phobia group identified by the phobia profile of the one of the users. The vehicle controller implements an alternate itinerary that mitigates the potential interaction.