HipChat's room feature is great, but what if I want to have an ad hoc conversation with two or more people? Does every group chat have to occur in a room?  If so, can a room be created such that people move in and out but are not members?

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Currently all multi-person chats in HipChat must occur in rooms. However, we've had a few suggestions to support ad-hoc chats without the overhead of creating a room. For example: https://jira.atlassian.com/browse/HCPUB-1856. You can go to that issue and vote / watch / comment in order to receive updates.

If you're just looking to have a place where people can enter and exit without being a "permament" room member, then it sounds like a public room might work for your purposes. You can quickly create one by using the keyboard shortcut CMD-SHIFT-N and then invite whoever you want to chat with with CMD-I. It's not quite the same, since the room requires a name, but it might help remove some of the overhead and get you close.

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