A system and method for connecting pending and preset telephone calls to facilitate transitioning to a phone call. Embodiments of the present invention include a method for anticipating and connecting a telephone call comprising identifying a trigger action associated with an anticipated outgoing telephone call, retrieving a phone number associated with said trigger action, and automatically setting a programmable speed dial button wherein by selecting the speed dial button, said phone number associated with said trigger action is dialed. Embodiments of the present invention also include a system for anticipating and connecting outgoing telephone calls comprising a computer system comprising a processor coupled to a bus, a database coupled to said bus, a call engine coupled to said bus wherein said call engine identifies trigger actions associated with outgoing telephone calls and retrieves phone numbers associated with said trigger actions, and a telephone coupled to said computer system wherein said telephone is coupled to a telephone network.