Communication connectivity via context association is provided by associating targeted subscriber contact information with a key at a subscriber database. At a data center, the keys are associated with unique characteristics or aliases (contexts) of the subscribers, thereby facilitating context searching. A caller initiates a connection to a subscriber by providing a subscriber's context. The context is located and associated key identified. The key is resolved in the subscriber database, and the call routed. Use of the key allows subscriber connectivity without revealing, to the caller or to the data center, sensitive contact information. Through a caller database, call initiation occurs by subscriber alias identification in a caller's communication device; thereby foregoing inclusion of sensitive contact information within the caller's communication device. Communication connectivity can be advertiser sponsored, with advertisements accompanying messages selected by matching profile information of targeted subscribers with participating advertiser provided profile information of desired targeted subscribers.