A proximity of a first computing device with a second computing device can be detected. In response to the detecting of the proximity, it can be determined that a computer-readable qualification for a type of proactive engagement is met using the detected proximity and possibly a non-proximity state of the first device. The type of proactive engagement can be matched in the computer system with an operation that is programmed to be performed using a computerized natural language digital assistant. In response to the determining that the qualification for the type of proactive engagement is met, the technique can include performing a user engagement action via the second device. The user engagement action can be of a type indicated by the type of proactive engagement. The user engagement action can facilitate a computerized communication session between a computer-readable user profile and the computerized natural language digital assistant.