A technique for initiating a communication session can include receiving a signal that a first and second user desire to participate in a communication session during a particular time period. The technique can include monitoring activity of the first and second users during the particular time period to determine whether the users are prepared to participate in the communication session. When it is determined that the first user is prepared to participate in the communication session, the technique can include outputting, to the second user computing device, an indication that the first user is prepared to participate in the communication session. When it is determined that both of the first and second users are prepared to participate in the communication session, the technique can include initiating the communication session.