A technique is disclosed that enables a context-driven, adaptive technique for generating a list of telephone numbers. The technique of the illustrative embodiment of the present invention seeks to dynamically anticipate what telephone numbers a user might want to dial—even before the user knows—and presents the names of the parties and their telephone numbers to the user at his or her terminal. In particular, the technique monitors a user, the user's locale, and one or more terminals in that locale; selects one or more telephone numbers from a master set of numbers, based on the monitored information; and presents the selected numbers to the user—for example, in the form of a speed-dial list or a one-touch dial list. The user can then examine the presented telephone numbers and decide if he or she wants to call one of them. The technique can be implemented at the user's computer, telephone, private branch exchange, or other device in the relevant telecommunications system.