Examples provide a system and method for initiating contactless communication sessions between computing devices using a variety of modalities. A user pre-registers a selected modality for triggering session initiation. A session initiation device generates trigger data based on a detected occurrence of a predetermined event corresponding to a user selected modality, such as, but not limited to, biometric data, a unique user identifier (ID), a vehicle identifier, or any other type of modality. The trigger data is mapped to a mobile device ID. The mobile device ID can be requested from a connection server. The communication session is established between the first computing device and the mobile user device using the mobile device identifier. The computing device transmits data to the mobile user device via the established communication session when the computing device is brought into proximity to the mobile user device.