I tried every single thing on this forum. Called apple support and even took it in to be serviced. The watch was a brick. I remembered that i had at one point enrolled in the apple beta years ago to get a new feature.
after unenrolling from this and syncing the watch it worked the first time. To test if this was the issue i enabled it again and tried and i ran in the same ****** issue. Unenrolled and bam it worked.
the apple beta causes this to happen for some watches it seems.
no where on my phone did it show i was in the beta I had to go to https://beta.apple.com/sp/betaprogram sign in and then click the unenroll link.
Amazing job apple. I had tried pairing with 5 different iphones on 3 different networks across 2 contents. Apple support was sure it was a router reboot that would do the trick lol.
I solved this issue by uninstalling the Watch app from my iphone and reloading it. After reloading the app I paired the watch to the phone and the update started loading.
I will say one thing today was a frustrating day trying to get the watch to pair for a few hours. Finally I have success. My fix is the same as many but it took only one try when I changed the Country and Language. I decided to use language Portuguese, and country Afghanistan. It worked. so mad I could not see straight. But success, hope it works for you. It will.
Apple Watch 3, iPhone 11Pro w/ iOS 14.6 - nothing works to update the watch and make it a usable device, it's basically a dud now. I've tried resetting the iPhone and trying to update the watch in different language. No dice!