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your db is messed up, could have happened if you unplugged your kobo without ejecting it properly.
go to your menu on the kobo and advanced and factory reset.
when that's done fill out the info and plug it into the pc and calibre will detect your device and you will be able to send books to and delete books from your device.
be sure to eject properly from the pc or calibre.
to eject properly go to my computer and find kobo reader, right click it and click on eject.
i've come across this several times but have a good system now, haven't had any problems since i started doing it this way.
hope that helps.
unfortunately you'll have to reload any books that you've had on there already but that really is no biggy if they're all loaded in calibre already.
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