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1.
A sub-Skype chat that develops as a result of two or more individuals that are participating in a Skype chat start their own chat while remaining in original chat
Lynne, Jonathan and Mark are side-skyping the HEY chat.
by Cortney B November 15, 2007
 
2.
a conversation on skype between two people that has spawned from another, larger skype conversation
(usually talking about person(s) in the aforementioned conversation)
so when Chase and Dalton started fighting on skype, Zach and I started side-skyping about why they kept this going after so long
by Patrick Awesome August 20, 2010