A method for real time digital instant messaging includes monitoring a condition of a wireless headset, estimating a potential for the user to receive and immediately respond to a real time digital message, such as an instant communications or a VoIP message, and then selectively directing a real time digital message, when received, to the user via the headset when the estimated potential indicates that the user is reasonably likely to immediately respond to the real time digital message. A sensor in the headset may be used to determine if a recent action of the user was don the headset by putting it on, doff the headset by taking it off, dock the headset by placing it in a charging station, move while wearing the headset, leave the headset on a desktop or other surface or carry the headset.