Skype sleep
v. To create a Skype connection with a faraway partner and then fall asleep together.
Skype sleeping pp.

Example Citations:
Kaj Hasselriis brings us the sweet story of a couple who "Skype Sleep", that is keeping their laptops on all night and falling asleep together on Skype.
—Nora Young, "Spark 161 - November 6 & 9, 2011," CBC Radio, November 6, 2011

Another tip for Skype-sleeping would to leave a night light or a bedside lamp on so you don't appear as a black block on the screen.
—"Looking at You Looking at Me," Glimmerbomb, February 28, 2012

Earliest Citation:
Skype sleep
Going to sleep with your laptop open next to your pillow and running Skype and watching your girlfriend or boyfriend, who is doing the same.
—"Skype sleep," Urban Dictionary, October 8, 2010

Notes:
Many thanks to the fabulous Karen H. for spying this term.

The more general practice of leaving a Skype connection open is known as ambient Skype:

For the first time in my life I used a Skype video call with my wife today as an ambient backdrop to life, rather than just as tool for having a conversation. I'd always wanted to try it, ever since hearing my friend and colleague Dave Newbold mention, in a presentation he was giving a couple of years ago about the near future for technology and social interaction, something he'd heard described as 'ambient Skype', whereby people leave a voice client running in the background while they are away from home as a way of being almost-there.
—Roo Reynolds, "Ambient Skype," Roo Reynolds - What's Next?," March 12, 2008

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