An apparatus, method and system provide for conditional answering in multiple leg telecommunication sessions, such as in a flexible alerting service. The preferred system includes a home location register (HLR) coupled to a mobile switching center (MSC). The HLR has, stored in a memory, a plurality of secondary directory numbers associated with a primary directory number, such as an ANSI compatible pilot directory number. The MSC has an interface for receiving an incoming call leg designating the primary directory number and for processing and routing each outgoing call leg associated with each secondary directory number. Following reception of a directive from the HLR, the MSC obtains information from a calling party to create called party information. When an outgoing call leg has been conditionally answered, the MSC provides the called party information on the conditionally answered outgoing call leg. Upon reception of the information, the called party may decide to accept the call, through an unconditional answer, or may hold or release the call. In the preferred embodiment, the called party information may include options or selections entered by the calling party, the name of the calling party, routing information, language selections, and product or service selections. Following an unconditional answer of an outgoing call leg, the MSC provides a connection between the unconditionally answered outgoing call leg and the incoming call leg to form a communication session.