Systems and methods for scheduling appointments are provided. This scheduling process includes generating an introductory message proposing an appointment with the target with a request for timing. The target responds, and this response is processed for a positive interest and the presence of a proposed time. If there is an absence of positive interest then the messaging may be discontinued. However, in the presence of a positive interest, and a proposed time from the target, the system may access an external scheduling system when a proposed time is present. This includes determining availability of at least one resource at the proposed time. The system then iteratively provides suggested times close to the proposed time when the resource is not available for the proposed time. The system then confirms the appointment when the resource is available for either the proposed time or any of the suggested times.