A meeting system facilitates spontaneous social encounter between users with a meeting server. The meeting server obtains calendar data and user preferences associated with each user of a plurality of users. The meeting server also prompts a first user device associated with a first user, and a second user device associated with a second user, for a social encounter based on the calendar data and the user preferences. Responsive to obtaining acceptances from the first user and the second user, the meeting server facilitates the social encounter between the first user and the second user.