Method and apparatus for initiating and managing a chat session are described herein. According to one embodiment, user activities with respect to the data processing system are monitored, including user activities that are unrelated to chat services. In response to a request to initiate a chat session between a local user and a remote user, a first chat service account is selected from a list of chat service accounts associated with the remote user based on the monitored user activities. A chat session is initiated using the selected first chat service account of the remote user and a second chat service account selected for the local user. Certain information is displayed within a chat window indicating that the chat session is conducted between the first and second chat service accounts. Other methods and apparatuses are also described.