The Wi-Fi walkman is a mobile multimedia application that we developed to investigate the technological and usability aspects of human-computer interaction with personalized, intelligent and context-aware wearable devices in peer-to-peer wireless environments such as the future home, office, or university campuses. It is a small handheld device with a wireless link that contains music content. Users carry their own walkman around and listen to music. All this music content is distributed in the peer-to-peer network and is shared using ad-hoc networking. The walkman naturally interacts with the users and users’ interest with each other in a peer-to-peer environment. Without annoying interactions, it can learn the users’ music interest/taste and consequently provide personalized music recommendation according to the current situated context and user’s interest.