There's a really quick way to send someone a new message even when you can't find them in your most recent conversation history. No matter where your focus is within the Skype window you can use CTRL+N, November, to open a new conversation.
Please allow [01:32] to watch the following instructional demonstration on starting a new conversation in Skype before continuing to the next topic.
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-01-70pix.png "Transcript - New Conversations in Skype"){kind=tracking}