I’m having the exact same problem. I didn’t use my apple watch (series 5) for a while, and I upgraded my iPhone XS to ios 14. I tried to pair my watch to my phone it didn’t pair. then I reseted my watch to reset it as a new watch, it told me that a software update is available for my watch and I should do the update to continue setting it up. when I tried to update it the “unable to check for update because you are not connected to the internet” message poped up. I’m 100% connected to the internet. I tried everything I found on the web and nothing works. trying to find an iphone with 13 ios to do the trick and see if it works. any updates on this problem by far? I am so sad and frustrated...