I have the same issue with a brand new apple watch series 5 and iOS 14.0.1. I got error “Unable to Check for update, your phone is not connected to the internet.” It’s just infinite loop from there.  I tried using iphone 6s and 8, both are running newest iOS 14.0.1 and I got the same error. I don’t have other iphone running older iOS. 

I have the same issue with a brand new apple watch series 5 and iOS 14.0.1. I got error “Unable to Check for update, your phone is not connected to the internet.” It’s just infinite loop from there.  I tried using iphone 6s and 8, both are running newest iOS 14.0.1 and I got the same error. I don’t have other iphone running older iOS.

I have this problem with a brand new Apple Watch series 5 and iOS 14.0.1. I cannot pair and update it. I don’t have iphone with iOS 13 nearby :(

I fixed it but I needed to borrow my friend’s iphone with iOS 13. After doing pair -> setup -> unpair on my friend’s iphone, I could finally paired and updated the watchOS from my iPhone iOS 14.

I fixed it but I needed to borrow my friend’s iphone with iOS 13. After doing pair -> setup -> unpair on my friend’s iphone, I could finally paired and updated the watchOS from my iPhone iOS 14. Or maybe Apple finally fixed it on their server end though. Either way I’m glad I can finally use it.

I had another brand new apple watch series 5 that couldn't pair with iOS 14, but after a few tries, I somehow manage to pair & update without using other iphone with iOS 13. Here's what I did: At first, I got the same error message during pairing, "couldn't connect to the internet to update watchOS". Then I tried using only 2.4GHz wifi like I saw in the other thread, but that didn't work either. So after restoring 5GHz wifi, I tried pairing using another iphone with iOS14, and of course it still gave me the same error. But then I then restarted my original iphone. After it booted back up, I enabled airplane mode and tried to do the pairing step again, and suddenly I can update the watchOS to 7.0.1. After the watch is updated I can proceed to pairing and setup. I have no idea what worked, did the airplane mode did the trick? Or the iphone switching? Or the restarting? I swear I tried the same things before and none of it worked, but now it works so beats me... Apple better release iOS update or info soon.